EX-99.2 4 a992-ahlq218.htm EXHIBIT 99.2
Exhibit 99.2

| FINANCIAL SUPPLEMENT
| As of June 30, 2018
| Aspen Insurance Holdings Limited |
| This financial supplement is for information purposes only. It should be read in conjunction with other documents filed or to be filed by Aspen Insurance Holdings Limited with the United States Securities and Exchange Commission.
| www.aspen.co |
| Investor Contact: |
| Aspen Insurance Holdings Limited |
| Mark Jones, Senior Vice President, Investor Relations |
| T: +1 646 289 4945 |
| email: Mark.P.Jones@aspen.co |

1

| ASPEN INSURANCE HOLDINGS LIMITED |
Table Of Contents |
|  |  |  | Page
| Basis of Presentation | 1
| Financial Highlights | 2
| Consolidated Statements of Operations - Quarterly Results | 3
| Consolidated Statements of Operations - Year to Date Results | 4
| Consolidated Balance Sheets | 5
| Earnings Per Share and Book Value Per Share | 6
| Return on Average Equity | 7
| Consolidated Underwriting Results by Operating Segment | 8 - 9
| Operating Segment - Quarterly Results | 10 - 11
| Written and Earned Premiums by Segment and Lines of Business | 12
| Consolidated Statements of Changes in Shareholders' Equity | 13
| Consolidated Statements of Comprehensive Income | 14
| Condensed Consolidated Statements of Cash Flows | 15
| Reserves for Losses and Loss Adjustment Expenses | 16
| Reserves by Operating Segment | 17
| Prior Year Reserve Releases | 18
| Consolidated Investment Portfolio | 19
| Investment Analysis | 20
| Book Value Per Ordinary Share | 21
| Operating Income Reconciliation | 22
| Worldwide Natural Catastrophe Exposures | 23

| ASPEN INSURANCE HOLDINGS LIMITED |
Basis of Presentation |
Definitions and presentations: All financial information contained herein is unaudited except for information for the fiscal year ended December 31, 2017. Unless otherwise noted, all data is in U.S. dollar millions, except for per share amounts, percentages and ratio information.
In presenting Aspen's results, management has included and discussed certain "non-GAAP financial measures". Management believes that these non-GAAP measures, which may be defined differently by other companies, better explain Aspen's results of operations in a manner that allows for a more complete understanding of the underlying trends in Aspen's business. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP. The reconciliation of such non-GAAP financial measures to their respective most directly comparable GAAP financial measures is included in this financial supplement.
Operating income (a non-GAAP financial measure): Operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operational results excluding, as applicable, after-tax net realized and unrealized gains or losses, after-tax net foreign exchange gains or losses, including net realized and unrealized gains and losses from foreign exchange contracts, net realized gains or losses on investments, amortization of intangible assets and certain non-recurring income and expenses, including expenses associated with the Company's operational effectiveness and efficiency program. Operating income in the second quarter of 2018 excluded the make-whole payment associated with the partial redemption of Aspen's 6.0% Senior Notes due 2020. Operating income in the first half of 2017 excluded the issue costs associated with the redemption of the 7.401% Perpetual Non-Cumulative Preference Shares.
Aspen excludes these items above from its calculation of operating income because they are either not expected to recur and therefore are not reflective of underlying performance or the amount of these gains or losses is heavily influenced by, and fluctuates in part, according to the availability of market opportunities. Aspen believes these amounts are largely independent of its business and underwriting process and including them would distort the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables investors, analysts, rating agencies and other users of its financial information to more easily analyze Aspen's results of operations in a manner similar to how management analyzes Aspen's underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see page 22 for a reconciliation of net income to operating income.
Annualized operating return on average equity (“Operating ROE”) (a non-GAAP financial measure): Operating ROE is calculated using operating income, as defined above, and average equity is calculated as the arithmetic average on a monthly basis for the stated periods of shareholders' equity excluding the aggregate value of the liquidation preferences of our preference shares net of issuance costs and the total amount of non-controlling interest.
Aspen presents Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information. See page 22 for a reconciliation of operating income to net income and page 7 for a reconciliation of average shareholders' equity to average ordinary shareholders' equity.
Diluted book value per ordinary share (not a non-GAAP financial measure): Aspen has included diluted book value per ordinary share as it illustrates the effect on basic book value per share of dilutive securities thereby providing a better benchmark for comparison with other companies. Diluted book value per share is calculated using the treasury stock method as defined on page 21.
Diluted operating earnings per share and basic operating earnings per share (non-GAAP financial measures): Aspen believes that the presentation of diluted operating earnings per share and basic operating earnings per share supports meaningful comparison from period to period and the analysis of normal business operations. Diluted operating earnings per share and basic operating earnings per share are calculated by dividing operating income by the diluted or basic weighted average number of shares outstanding for the period. See page 22 for a reconciliation of basic earnings per share to diluted and basic operating earnings per share.
Accident year loss ratio excluding catastrophes (a non-GAAP financial measure): Aspen believes that the presentation of loss ratios excluding catastrophes and prior year reserve movements supports meaningful comparison from period to period of the underlying performance of the business. Accident year loss ratios excluding catastrophes are calculated by dividing net losses excluding catastrophe losses and prior year reserve movements by net earned premiums excluding catastrophe-related reinstatement premiums. Aspen has defined catastrophe losses in in the first half of 2018 as losses associated with Winter Storm Friederike in Europe and U.K and U.S. weather-related events. Catastrophe losses in the first half of 2017 were defined as losses associated predominantly with a tornado in Mississippi, Cyclone Debbie in Australia, and various other weather-related events. See pages 10 and 11 for a reconciliation of loss ratios to accident year loss ratios excluding catastrophes.
Underwriting ratios (GAAP financial measures): Aspen, along with others in the industry, uses underwriting ratios as measures of performance. The loss ratio is the ratio of net claims and claims adjustment expenses to net premiums earned. The acquisition expense ratio is the ratio of underwriting expenses (commissions, premium taxes, licenses and fees, as well as other underwriting expenses) to net premiums earned. The general and administrative expense ratio is the ratio of general and administrative expenses to net premiums earned. The combined ratio is the sum of the loss ratio, the acquisition expense ratio and the general and administrative expense ratio. These ratios are relative measurements that describe for every $100 of net premiums earned, the cost of losses and expenses, respectively. The combined ratio presents the total cost per $100 of earned premium. A combined ratio below 100% demonstrates underwriting profit; a combined ratio above 100% demonstrates underwriting loss.
GAAP combined ratios differ from U.S. statutory combined ratios primarily due to the deferral of certain third-party acquisition expenses for GAAP reporting purposes and the use of net premiums earned rather than net premiums written in the denominator when calculating the acquisition expense and the general and administrative expense ratios.

1

| ASPEN INSURANCE HOLDINGS LIMITED
Financial Highlights
|  |  |  | Three Months Ended June 30, |  | Six Months Ended June 30,
(in US$ millions except for percentages, share and per share amounts) |  | 2018 |  | 2017 |  | Change |  | 2018 |  | 2017 |  | Change
Gross written premium |  | $ | 853.8 |  |  | $ | 822.1 |  |  | 3.9 | % |  | $ | 1,970.6 |  |  | $ | 1,820.1 |  |  | 8.3 | %
Net written premium |  | $ | 486.0 |  |  | $ | 578.7 |  |  | (16.0 | )% |  | $ | 1,121.5 |  |  | $ | 1,264.9 |  |  | (11.3 | )%
Net earned premium |  | $ | 519.5 |  |  | $ | 562.0 |  |  | (7.6 | )% |  | $ | 1,053.0 |  |  | $ | 1,143.1 |  |  | (7.9 | )%
Net (loss)/income after tax |  | $ | (14.7 | ) |  | $ | 75.8 |  |  | (119.4 | )% |  | $ | 16.1 |  |  | $ | 172.3 |  |  | (90.7 | )%
Operating income after tax |  | $ | 56.3 |  |  | $ | 39.2 |  |  | 43.6 | % |  | $ | 119.3 |  |  | $ | 99.0 |  |  | 20.5 | %
Net investment income |  | $ | 50.4 |  |  | $ | 47.4 |  |  | 6.3 | % |  | $ | 97.7 |  |  | $ | 95.1 |  |  | 2.7 | %
Underwriting income |  | $ | 22.1 |  |  | $ | 1.8 |  |  | 1,127.8 | % |  | $ | 45.7 |  |  | $ | 21.9 |  |  | 108.7 | %
Earnings Per Share and Book Value Per Share |  |  |  |  |  |  |  |  |  |  |  |
Basic earnings per ordinary share |  |  |  |  |  |  |  |  |  |  |  |
Net (loss)/income adjusted for preference share dividend and non-controlling interest |  | $ | (0.38 | ) |  | $ | 1.09 |  |  | (134.9 | )% |  | $ | 0.01 |  |  | $ | 2.48 |  |  | (99.6 | )%
Operating income adjusted for preference share dividend and non-controlling interest |  | $ | 0.81 |  |  | $ | 0.48 |  |  | 68.8 | % |  | $ | 1.73 |  |  | $ | 1.29 |  |  | 34.1 | %
Diluted earnings per ordinary share |  |  |  |  |  |  |  |  |  |  |  |
Net (loss)/income adjusted for preference share dividend and non-controlling interest |  | $ | (0.38 | ) |  | $ | 1.07 |  |  | (135.5 | )% |  | $ | 0.01 |  |  | $ | 2.43 |  |  | (99.6 | )%
Operating income adjusted for preference share dividend and non-controlling interest |  | $ | 0.80 |  |  | $ | 0.47 |  |  | 70.2 | % |  | $ | 1.71 |  |  | $ | 1.27 |  |  | 34.6 | %
Weighted average number of ordinary shares outstanding (in millions of shares) (1) |  | 59.672 |  |  | 59.966 |  |  | (0.5 | )% |  | 59.609 |  |  | 59.915 |  |  | (0.5 | )%
Diluted weighted average number of ordinary shares outstanding (in millions of shares) |  | 59.672 |  |  | 61.023 |  |  | (2.2 | )% |  | 60.528 |  |  | 61.096 |  |  | (0.9 | )%
Book value per ordinary share |  | $ | 38.75 |  |  | $ | 49.34 |  |  | (21.5 | )% |  | $ | 38.75 |  |  | $ | 49.34 |  |  | (21.5 | )%
Diluted book value per ordinary share |  | $ | 38.21 |  |  | $ | 48.64 |  |  | (21.4 | )% |  | $ | 38.21 |  |  | $ | 48.64 |  |  | (21.4 | )%
Ordinary shares outstanding at June 30, 2018 and June 30, 2017 (in millions of shares) |  | 59.688 |  |  | 59.844 |  |  | (0.3 | )% |  | 59.688 |  |  | 59.844 |  |  | (0.3 | )%
Diluted ordinary shares outstanding at June 30, 2018 and June 30, 2017 (in millions of shares) |  | 60.534 |  |  | 60.712 |  |  | (0.3 | )% |  | 60.534 |  |  | 60.712 |  |  | (0.3 | )%
Underwriting Ratios |  |  |  |  |  |  |  |  |  |  |  |
Loss ratio |  | 59.7 | % |  | 61.6 | % |  |  |  | 58.9 | % |  | 59.0 | % |  |
Policy acquisition expense ratio |  | 16.5 | % |  | 17.1 | % |  |  |  | 16.8 | % |  | 18.4 | % |  |
General, administrative and corporate expense ratio |  | 21.2 | % |  | 21.3 | % |  |  |  | 22.0 | % |  | 21.1 | % |  |
General, administrative and corporate expense ratio (excluding amortization and non-recurring expenses) |  | 19.5 | % |  | 21.0 | % |  |  |  | 19.9 | % |  | 20.7 | % |  |
Expense ratio |  | 37.7 | % |  | 38.4 | % |  |  |  | 38.8 | % |  | 39.5 | % |  |
Expense ratio (excluding amortization and non-recurring expenses) |  | 36.0 | % |  | 38.1 | % |  |  |  | 36.7 | % |  | 39.1 | % |  |
Combined ratio |  | 97.4 | % |  | 100.0 | % |  |  |  | 97.7 | % |  | 98.5 | % |  |
Combined ratio (excluding amortization and non-recurring expenses) |  | 95.7 | % |  | 99.7 | % |  |  |  | 95.6 | % |  | 98.1 | % |  |
Return On Equity |  |  |  |  |  |  |  |  |  |  |  |
Average equity (2) |  | $ | 2,328.6 |  |  | $ | 2,939.8 |  |  |  |  | $ | 2,355.2 |  |  | $ | 2,930.9 |  |  |
Return on average equity |  |  |  |  |  |  |  |  |  |  |  |
Net (loss)/income adjusted for preference share dividend and non-controlling interest |  | (1.0 | )% |  | 2.2 | % |  |  |  | 0.03 | % |  | 5.1 | % |  |
Operating income adjusted for preference share dividend and non-controlling interest |  | 2.1 | % |  | 1.0 | % |  |  |  | 4.4 | % |  | 2.7 | % |  |
Annualized return on average equity |  |  |  |  |  |  |  |  |  |  |  |
Net (loss)/income |  | (4.0 | )% |  | 8.8 | % |  |  |  | 0.06 | % |  | 10.2 | % |  |
Operating income |  | 8.4 | % |  | 4.0 | % |  |  |  | 8.8 | % |  | 5.4 | % |  |
See pages 7 and 22 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. |  |  |  |  |  |
(1) The basic and diluted number of ordinary shares for the three and six months ended June 30, 2018 is the same, as the inclusion of dilutive securities in a loss-making period would be anti-dilutive. |  |  |  |
(2) Average equity excludes preference shares. |  |  |  |

2

| ASPEN INSURANCE HOLDINGS LIMITED
Consolidated Statements of Operations - Quarterly Results
(in US$ millions except for percentages) | Q2 2018 |  | Q1 2018 |  | Q4 2017 |  | Q3 2017 |  | Q2 2017 |  | Q1 2017
UNDERWRITING REVENUES |  |  |  |  |  |  |  |  |  |  |
Gross written premiums | $ | 853.8 |  |  | $ | 1,116.8 |  |  | $ | 688.3 |  |  | $ | 852.5 |  |  | $ | 822.1 |  |  | $ | 998.0 |
Premiums ceded | (367.8 | ) |  | (481.3 | ) |  | (348.1 | ) |  | (245.1 | ) |  | (243.4 | ) |  | (311.8 | )
Net written premiums | 486.0 |  |  | 635.5 |  |  | 340.2 |  |  | 607.4 |  |  | 578.7 |  |  | 686.2 |
Change in unearned premiums | 33.5 |  |  | (102.0 | ) |  | 170.8 |  |  | 45.1 |  |  | (16.7 | ) |  | (105.1 | )
Net earned premiums | 519.5 |  |  | 533.5 |  |  | 511.0 |  |  | 652.5 |  |  | 562.0 |  |  | 581.1 |
UNDERWRITING EXPENSES |  |  |  |  |  |  |  |  |  |  |
Losses and loss adjustment expenses | 310.4 |  |  | 310.2 |  |  | 544.2 |  |  | 776.2 |  |  | 346.1 |  |  | 328.2 |
Amortization of deferred policy acquisition costs | 85.9 |  |  | 90.8 |  |  | 85.1 |  |  | 105.4 |  |  | 96.3 |  |  | 113.7 |
General, administrative and corporate expenses | 101.1 |  |  | 108.9 |  |  | 126.9 |  |  | 105.7 |  |  | 117.8 |  |  | 119.1 |
Total underwriting expenses | 497.4 |  |  | 509.9 |  |  | 756.2 |  |  | 987.3 |  |  | 560.2 |  |  | 561.0 |
Underwriting income/(loss) including corporate expenses | 22.1 |  |  | 23.6 |  |  | (245.2 | ) |  | (334.8 | ) |  | 1.8 |  |  | 20.1 |
Net investment income | 50.4 |  |  | 47.3 |  |  | 47.5 |  |  | 46.4 |  |  | 47.4 |  |  | 47.7 |
Interest expense | (7.6 | ) |  | (7.4 | ) |  | (7.3 | ) |  | (7.4 | ) |  | (7.4 | ) |  | (7.4 | )
Other (expense)/income (1) | (1.8 | ) |  | 1.9 |  |  | 18.6 |  |  | 7.6 |  |  | (1.7 | ) |  | 0.7 |
Total other revenue | 41.0 |  |  | 41.8 |  |  | 58.8 |  |  | 46.6 |  |  | 38.3 |  |  | 41.0 |
Amortization and non-recurring expenses | (9.1 | ) |  | (12.1 | ) |  | (23.2 | ) |  | (5.2 | ) |  | (2.1 | ) |  | (2.2 | )
Net realized and unrealized exchange (losses)/gains (2) | (40.9 | ) |  | 18.8 |  |  | (0.3 | ) |  | 12.9 |  |  | (3.0 | ) |  | (5.8 | )
Net realized and unrealized investment (losses)/gains | (20.7 | ) |  | (37.7 | ) |  | 14.8 |  |  | 17.5 |  |  | 42.0 |  |  | 46.2 |
Realized (loss) on debt extinguishment | (8.6 | ) |  | — |  |  | — |  |  | — |  |  | — |  |  | — |
(LOSS)/INCOME BEFORE TAX | (16.2 | ) |  | 34.4 |  |  | (195.1 | ) |  | (263.0 | ) |  | 77.0 |  |  | 99.3 |
Income tax credit/(expense) | 1.5 |  |  | (3.6 | ) |  | 10.2 |  |  | 9.2 |  |  | (1.2 | ) |  | (2.8 | )
NET (LOSS)/INCOME AFTER TAX | (14.7 | ) |  | 30.8 |  |  | (184.9 | ) |  | (253.8 | ) |  | 75.8 |  |  | 96.5 |
Dividends paid on ordinary shares | (14.3 | ) |  | (14.3 | ) |  | (14.3 | ) |  | (14.4 | ) |  | (14.4 | ) |  | (13.2 | )
Dividends paid on preference shares | (7.6 | ) |  | (7.6 | ) |  | (7.5 | ) |  | (7.7 | ) |  | (10.5 | ) |  | (10.5 | )
Preference share redemption costs | — |  |  | — |  |  | — |  |  | (5.6 | ) |  | — |  |  | (2.4 | )
Proportion due to non-controlling interest | (0.1 | ) |  | (0.2 | ) |  | (0.5 | ) |  | (0.6 | ) |  | (0.1 | ) |  | (0.1 | )
Retained (loss)/income | $ | (36.7 | ) |  | $ | 8.7 |  |  | $ | (207.2 | ) |  | $ | (282.1 | ) |  | $ | 50.8 |  |  | $ | 70.3 |
Loss ratio | 59.7 | % |  | 58.1 | % |  | 106.5 | % |  | 119.0 | % |  | 61.6 | % |  | 56.5 | %
Policy acquisition expense ratio | 16.5 | % |  | 17.0 | % |  | 16.7 | % |  | 16.2 | % |  | 17.1 | % |  | 19.6 | %
General, administrative and corporate expense ratio | 21.2 | % |  | 22.7 | % |  | 29.4 | % |  | 17.0 | % |  | 21.3 | % |  | 20.9 | %
General, administrative and corporate expense ratio (excluding amortization and non-recurring expenses) | 19.5 | % |  | 20.4 | % |  | 24.8 | % |  | 16.2 | % |  | 21.0 | % |  | 20.5 | %
Expense ratio | 37.7 | % |  | 39.7 | % |  | 46.1 | % |  | 33.2 | % |  | 38.4 | % |  | 40.5 | %
Expense ratio (excluding amortization and non-recurring expenses) | 36.0 | % |  | 37.4 | % |  | 41.5 | % |  | 32.4 | % |  | 38.1 | % |  | 40.1 | %
Combined ratio | 97.4 | % |  | 97.8 | % |  | 152.6 | % |  | 152.2 | % |  | 100.0 | % |  | 97.0 | %
Combined ratio (excluding amortization and non-recurring expenses) | 95.7 | % |  | 95.5 | % |  | 148.0 | % |  | 151.4 | % |  | 99.7 | % |  | 96.6 | %
See pages 7 and 22 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.
(1) Other (expense) income in the second quarter of 2018 and second quarter of 2017 included expenses of $3.4 million and $3.3 million, respectively, related to a change in the fair value of loan notes issued by Silverton Re.
(2) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.

3

| ASPEN INSURANCE HOLDINGS LIMITED
Consolidated Statements of Operations - Year To Date Results
(in US$ millions except for percentages) |  | Six Months Ended June 30,
|  | 2018 |  | 2017
UNDERWRITING REVENUES |  |  |
Gross written premiums |  | $ | 1,970.6 |  |  | $ | 1,820.1 |
Premiums ceded |  | (849.1 | ) |  | (555.2 | )
Net written premiums |  | 1,121.5 |  |  | 1,264.9 |
Change in unearned premiums |  | (68.5 | ) |  | (121.8 | )
Net earned premiums |  | 1,053.0 |  |  | 1,143.1 |
UNDERWRITING EXPENSES |  |  |  |
Losses and loss adjustment expenses |  | 620.6 |  |  | 674.3 |
Amortization of deferred policy acquisition costs |  | 176.7 |  |  | 210.0 |
General, administrative and corporate expenses |  | 210.0 |  |  | 236.9 |
Total underwriting expenses |  | 1,007.3 |  |  | 1,121.2 |
Underwriting income including corporate expenses |  | 45.7 |  |  | 21.9 |
Net investment income |  | 97.7 |  |  | 95.1 |
Interest expense |  | (15.0 | ) |  | (14.8 | )
Other income/(expense) |  | 0.1 |  |  | (1.0 | )
Total other revenue |  | 82.8 |  |  | 79.3 |
Amortization and non-recurring expenses |  | (21.2 | ) |  | (4.3 | )
Net realized and unrealized exchange (losses) (1) |  | (22.1 | ) |  | (8.8 | )
Net realized and unrealized investment (losses)/gains |  | (58.4 | ) |  | 88.2 |
Realized (loss) on debt extinguishment |  | (8.6 | ) |  | — |
INCOME BEFORE TAX |  | 18.2 |  |  | 176.3 |
Income tax expense |  | (2.1 | ) |  | (4.0 | )
NET INCOME AFTER TAX |  | 16.1 |  |  | 172.3 |
Dividends paid on ordinary shares |  | (28.6 | ) |  | (27.6 | )
Dividends paid on preference shares |  | (15.2 | ) |  | (21.0 | )
Preference share redemption costs |  | — |  |  | (2.4 | )
Proportion due to non-controlling interest |  | (0.3 | ) |  | (0.2 | )
Retained (loss)/income |  | $ | (28.0 | ) |  | $ | 121.1 |
Loss ratio |  | 58.9 | % |  | 59.0 | %
| Policy acquisition expense ratio |  | 16.8 | % |  | 18.4 | %
| General, administrative and corporate expense ratio |  | 22.0 | % |  | 21.1 | %
| General, administrative and corporate expense ratio (excluding amortization and non-recurring expenses) |  | 19.9 | % |  | 20.7 | %
Expense ratio |  | 38.8 | % |  | 39.5 | %
Expense ratio (excluding amortization and non-recurring expenses) |  | 36.7 | % |  | 39.1 | %
Combined ratio |  | 97.7 | % |  | 98.5 | %
Combined ratio (excluding amortization and non-recurring expenses) |  | 95.6 | % |  | 98.1 | %
See pages 7 and 22 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.
(1) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.

4

| Consolidated Balance Sheets
| (in US$ millions except for per share amounts) |  | June 30, 2018 |  | March 31, 2018 |  | December 31, 2017 |  | September 30, 2017 |  | June 30, 2017 |  | March 31, 2017 |
| Investments |  |  |  |  |  |  |  |  |  |  |  |  |
| Fixed income securities |  | $ | 6,695.9 |  |  | $ | 7,049.8 |  |  | $ | 6,880.3 |  |  | $ | 7,030.4 |  |  | $ | 6,854.8 |  |  | $ | 6,977.6 |  |
| Equity securities |  | — |  |  | — |  |  | 491.0 |  |  | 468.6 |  |  | 658.7 |  |  | 623.6 |  |
| Other investments |  | 153.3 |  |  | 66.1 |  |  | 66.4 |  |  | 4.0 |  |  | 3.9 |  |  | 5.0 |  |
| Catastrophe bonds |  | 35.5 |  |  | 34.8 |  |  | 32.4 |  |  | 30.3 |  |  | 28.3 |  |  | 41.8 |  |
| Short-term investments |  | 99.6 |  |  | 81.6 |  |  | 162.9 |  |  | 124.7 |  |  | 115.6 |  |  | 348.1 |  |
| Total investments |  | 6,984.3 |  |  | 7,232.3 |  |  | 7,633.0 |  |  | 7,658.0 |  |  | 7,661.3 |  |  | 7,996.1 |  |
| Cash and cash equivalents |  | 1,070.7 |  |  | 1,246.9 |  |  | 1,054.8 |  |  | 1,209.3 |  |  | 1,228.4 |  |  | 873.1 |  |
| Reinsurance recoverables |  |  |  |  |  |  |  |  |  |  |  |  |
| Unpaid losses |  | 1,656.4 |  |  | 1,611.3 |  |  | 1,515.2 |  |  | 1,369.5 |  |  | 779.4 |  |  | 635.8 |  |
| Ceded unearned premiums |  | 724.8 |  |  | 683.9 |  |  | 515.5 |  |  | 446.4 |  |  | 464.1 |  |  | 404.8 |  |
| Receivables |  |  |  |  |  |  |  |  |  |  |  |  |
| Underwriting premiums |  | 1,725.2 |  |  | 1,743.0 |  |  | 1,496.5 |  |  | 1,529.0 |  |  | 1,614.1 |  |  | 1,557.8 |  |
| Other |  | 175.5 |  |  | 108.6 |  |  | 151.1 |  |  | 175.8 |  |  | 106.1 |  |  | 120.7 |  |
| Funds withheld |  | 89.3 |  |  | 102.9 |  |  | 99.8 |  |  | 100.1 |  |  | 89.9 |  |  | 90.4 |  |
| Deferred policy acquisition costs |  | 298.6 |  |  | 319.9 |  |  | 294.3 |  |  | 354.1 |  |  | 364.6 |  |  | 367.5 |  |
| Derivatives at fair value |  | 14.1 |  |  | 15.6 |  |  | 6.4 |  |  | 8.4 |  |  | 22.1 |  |  | 5.2 |  |
| Receivable for securities sold |  | 2.6 |  |  | 4.1 |  |  | 5.3 |  |  | 19.0 |  |  | 13.6 |  |  | 25.7 |  |
| Office properties and equipment |  | 73.0 |  |  | 77.1 |  |  | 75.5 |  |  | 89.8 |  |  | 85.3 |  |  | 86.1 |  |
| Taxation |  | 32.7 |  |  | 34.3 |  |  | 30.6 |  |  | 13.1 |  |  | 7.2 |  |  | — |  |
| Other assets |  | 0.5 |  |  | 0.5 |  |  | 0.5 |  |  | 1.0 |  |  | 1.0 |  |  | 1.0 |  |
| Intangible assets and goodwill |  | 27.0 |  |  | 27.5 |  |  | 27.9 |  |  | 78.1 |  |  | 79.4 |  |  | 80.5 |  |
| Total assets |  | $ | 12,874.7 |  |  | $ | 13,207.9 |  |  | $ | 12,906.4 |  |  | $ | 13,051.6 |  |  | $ | 12,516.5 |  |  | $ | 12,244.7 |  |
| LIABILITIES |  |  |  |  |  |  |  |  |  |  |  |  |
| Insurance reserves |  |  |  |  |  |  |  |  |  |  |  |  |
| Losses and loss adjustment expenses |  | $ | 6,532.8 |  |  | $ | 6,679.4 |  |  | $ | 6,749.5 |  |  | $ | 6,490.6 |  |  | $ | 5,571.4 |  |  | $ | 5,365.9 |  |
| Unearned premiums |  | 2,087.2 |  |  | 2,097.7 |  |  | 1,820.8 |  |  | 1,926.5 |  |  | 1,981.5 |  |  | 1,891.8 |  |
| Total insurance reserves |  | 8,620.0 |  |  | 8,777.1 |  |  | 8,570.3 |  |  | 8,417.1 |  |  | 7,552.9 |  |  | 7,257.7 |  |
| Payables |  |  |  |  |  |  |  |  |  |  |  |  |
| Reinsurance premiums |  | 596.0 |  |  | 491.3 |  |  | 357.5 |  |  | 439.4 |  |  | 316.7 |  |  | 362.9 |  |
| Taxation |  | — |  |  | — |  |  | — |  |  | 0.5 |  |  | 4.4 |  |  | 4.0 |  |
| Accrued expenses and other payables |  | 336.5 |  |  | 496.5 |  |  | 455.4 |  |  | 377.9 |  |  | 352.8 |  |  | 361.8 |  |
| Liabilities under derivative contracts |  | 49.3 |  |  | 2.3 |  |  | 1.0 |  |  | 2.9 |  |  | 8.6 |  |  | 4.3 |  |
| Total payables |  | 981.8 |  |  | 990.1 |  |  | 813.9 |  |  | 820.7 |  |  | 682.5 |  |  | 733.0 |  |
| Loan notes issued by variable interest entities, at fair value |  | 20.3 |  |  | 32.2 |  |  | 44.2 |  |  | 101.5 |  |  | 110.8 |  |  | 110.2 |  |
| Long-term debt |  | 424.6 |  |  | 549.5 |  |  | 549.5 |  |  | 549.4 |  |  | 549.4 |  |  | 549.4 |  |
| Total liabilities |  | 10,046.7 |  |  | 10,348.9 |  |  | 9,977.9 |  |  | 9,888.7 |  |  | 8,895.6 |  |  | 8,650.3 |  |
| SHAREHOLDERS’ EQUITY |  |  |  |  |  |  |  |  |  |  |  |  |
| Ordinary shares |  | 0.1 |  |  | 0.1 |  |  | 0.1 |  |  | 0.1 |  |  | 0.1 |  |  | 0.1 |  |
| Non-controlling interest |  | 3.0 |  |  | 2.9 |  |  | 2.7 |  |  | 2.2 |  |  | 1.6 |  |  | 1.5 |  |
| Preference shares |  | — |  |  | — |  |  | — |  |  | — |  |  | — |  |  | — |  |
| Additional paid-in capital |  | 965.4 |  |  | 959.5 |  |  | 954.7 |  |  | 951.8 |  |  | 1,125.2 |  |  | 1,142.1 |  |
| Retained earnings |  | 1,998.9 |  |  | 2,035.6 |  |  | 2,026.9 |  |  | 2,234.1 |  |  | 2,516.2 |  |  | 2,465.4 |  |
| Accumulated other comprehensive income, net of taxes |  | (139.4 | ) |  | (139.1 | ) |  | (55.9 | ) |  | (25.3 | ) |  | (22.2 | ) |  | (14.7 | ) |
| Total shareholders’ equity |  | 2,828.0 |  |  | 2,859.0 |  |  | 2,928.5 |  |  | 3,162.9 |  |  | 3,620.9 |  |  | 3,594.4 |  |
| Total liabilities and shareholders’ equity |  | $ | 12,874.7 |  |  | $ | 13,207.9 |  |  | $ | 12,906.4 |  |  | $ | 13,051.6 |  |  | $ | 12,516.5 |  |  | $ | 12,244.7 |  |
| Book value per ordinary share |  | $ | 38.75 |  |  | $ | 39.30 |  |  | $ | 40.59 |  |  | $ | 44.59 |  |  | $ | 49.34 |  |  | $ | 48.79 |  |
| Book value per diluted ordinary share |  | $ | 38.21 |  |  | $ | 38.70 |  |  | $ | 40.10 |  |  | $ | 44.00 |  |  | $ | 48.64 |  |  | $ | 47.89 |  |

5

| ASPEN INSURANCE HOLDINGS LIMITED
Earnings Per Share and Book Value Per Share
|  |  |  | Three Months Ended |  | Six Months Ended
(in US$ except for number of shares) |  | June 30, 2018 |  | June 30, 2017 |  | June 30, 2018 |  | June 30, 2017
Basic earnings per ordinary share |  |  |  |  |  |  |  |
| Net (loss)/income adjusted for preference share dividend and non-controlling interest |  | $ | (0.38 | ) |  | $ | 1.09 |  |  | $ | 0.01 |  |  | $ | 2.48 |
| Operating income adjusted for preference share dividend and non-controlling interest |  | $ | 0.81 |  |  | $ | 0.48 |  |  | $ | 1.73 |  |  | $ | 1.29 |
Diluted earnings per ordinary share |  |  |  |  |  |  |  |
| Net (loss)/income adjusted for preference share dividend and non-controlling interest |  | $ | (0.38 | ) |  | $ | 1.07 |  |  | $ | 0.01 |  |  | $ | 2.43 |
| Operating income adjusted for preference share dividend and non-controlling interest |  | $ | 0.80 |  |  | $ | 0.47 |  |  | $ | 1.71 |  |  | $ | 1.27 |
Weighted average number of ordinary shares outstanding (in millions) |  | 59.672 |  |  | 59.966 |  |  | 59.609 |  |  | 59.915 |
Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions) |  | 59.672 |  |  | 61.023 |  |  | 60.528 |  |  | 61.096 |
Book value per ordinary share |  | $ | 38.75 |  |  | $ | 49.34 |  |  | $ | 38.75 |  |  | $ | 49.34 |
Diluted book value per ordinary share |  | $ | 38.21 |  |  | $ | 48.64 |  |  | $ | 38.21 |  |  | $ | 48.64 |
Ordinary shares outstanding at end of the period (in millions) |  | 59.688 |  |  | 59.844 |  |  | 59.688 |  |  | 59.844 |
Ordinary shares outstanding and dilutive potential ordinary shares at end of the period (in millions) |  | 60.534 |  |  | 60.712 |  |  | 60.534 |  |  | 60.712 |
See pages 7 and 22 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures.
(1) The basic and diluted number of ordinary shares for the three months ended June 30, 2018 is the same, as the inclusion of dilutive securities in a loss-making period would be anti-dilutive.

6

| ASPEN INSURANCE HOLDINGS LIMITED |  |  |  |
Return On Average Equity |  |  |  |
|  |  |  | Three Months Ended |  | Six Months Ended
(in US$ millions except for percentages) |  | June 30, 2018 |  | June 30, 2017 |  | June 30, 2018 |  | June 30, 2017
Average shareholders' equity | $ | 2,843.5 |  |  | $ | 3,607.7 |  |  | $ | 2,870.0 |  |  | $ | 3,617.4 |
Average non-controlling interest | (3.0 | ) |  | (1.6 | ) |  | (2.9 | ) |  | (1.5 | )
Average preference shares | (511.9 | ) |  | (666.3 | ) |  | (511.9 | ) |  | (685.0 | )
Average ordinary shareholders' equity | $ | 2,328.6 |  |  | $ | 2,939.8 |  |  | $ | 2,355.2 |  |  | $ | 2,930.9 |
Return on average equity: |  |  |  |  |  |  |
| Net (loss)/income adjusted for preference share dividend and non-controlling interest | (1.0 | )% |  | 2.2 | % |  | 0.03 | % |  | 5.1 | %
| Operating income adjusted for preference share dividend and non-controlling interest | 2.1 | % |  | 1.0 | % |  | 4.4 | % |  | 2.7 | %
Annualized return on average equity: |  |  |  |  |  |  |
| Net (loss)/income | (4.0 | )% |  | 8.8 | % |  | 0.06 | % |  | 10.2 | %
| Operating income |  | 8.4 | % |  | 4.0 | % |  | 8.8 | % |  | 5.4 | %
Components of return on average equity: |  |  |  |  |  |  |
| Return on average equity from underwriting activity (1) | 0.9 | % |  | 0.1 | % |  | 1.9 | % |  | 0.5 | %
| Return on average equity from investment and other activity (2) | 1.4 | % |  | 0.9 | % |  | 2.9 | % |  | 2.3 | %
| Pre-tax operating income return on average equity (3) | 2.4 | % |  | 1.0 | % |  | 4.8 | % |  | 2.8 | %
| Post-tax operating income return on average equity (4) | 2.1 | % |  | 1.0 | % |  | 4.4 | % |  | 2.7 | %
See page 22 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. |  |  |  |
(1) Calculated by using underwriting income. |  |  |  |
(2) Calculated by using total other operating revenue and other income/(expense) adjusted for preference share dividends and non-controlling interest. |  |  |  |
(3) Calculated by using operating income before tax adjusted for preference share dividends and non-controlling interest. |  |  |  |
(4) Calculated by using operating income after-tax adjusted for preference share dividends and non-controlling interest. |  |  |  |

7

| ASPEN INSURANCE HOLDINGS LIMITED |  |
Consolidated Underwriting Results by Operating Segment |  |
|  |  | Three Months Ended June 30, 2018 |  | Three Months Ended June 30, 2017
(in US$ millions except for percentages) | Reinsurance |  | Insurance |  | Total |  | Reinsurance |  | Insurance |  | Total
Gross written premiums | $ | 326.0 |  |  | $ | 527.8 |  |  | $ | 853.8 |  |  | $ | 335.6 |  |  | $ | 486.5 |  |  | $ | 822.1 |
Net written premiums | 266.9 |  |  | 219.1 |  |  | 486.0 |  |  | 285.5 |  |  | 293.2 |  |  | 578.7 |
Gross earned premiums | 366.2 |  |  | 479.3 |  |  | 845.5 |  |  | 320.6 |  |  | 429.1 |  |  | 749.7 |
Net earned premiums | 289.0 |  |  | 230.5 |  |  | 519.5 |  |  | 272.7 |  |  | 289.3 |  |  | 562.0 |
Losses and loss adjustment expenses | 167.0 |  |  | 143.4 |  |  | 310.4 |  |  | 152.6 |  |  | 193.5 |  |  | 346.1 |
Amortization of deferred policy acquisition costs | 62.8 |  |  | 23.1 |  |  | 85.9 |  |  | 53.4 |  |  | 42.9 |  |  | 96.3 |
General and administrative expenses | 27.9 |  |  | 57.2 |  |  | 85.1 |  |  | 40.7 |  |  | 65.7 |  |  | 106.4 |
Underwriting income/(loss) | $ | 31.3 |  |  | $ | 6.8 |  |  | $ | 38.1 |  |  | $ | 26.0 |  |  | $ | (12.8 | ) |  | $ | 13.2 |
Net investment income |  |  |  |  | 50.4 |  |  |  |  |  |  | 47.4 |
Net realized and unrealized investment (losses)/gains |  |  |  |  | (20.7 | ) |  |  |  |  |  | 42.0 |
Realized (loss) on debt extinguishment |  |  |  |  | (8.6 | ) |  |  |  |  |  | — |
Corporate expenses |  |  |  |  | (16.0 | ) |  |  |  |  |  | (11.4 | )
Amortization and non-recurring expenses (1) |  |  |  |  | (9.1 | ) |  |  |  |  |  | (2.1 | )
Other (expense)/income(2) |  |  |  |  | (1.8 | ) |  |  |  |  |  | (1.7 | )
Interest expense |  |  |  |  | (7.6 | ) |  |  |  |  |  | (7.4 | )
Net realized and unrealized foreign exchange (losses)(3) |  |  |  |  | (40.9 | ) |  |  |  |  |  | (3.0 | )
(Loss)/income before tax |  |  |  |  | $ | (16.2 | ) |  |  |  |  |  | $ | 77.0 |
Income tax credit/(expense) |  |  |  |  | 1.5 |  |  |  |  |  |  | (1.2 | )
Net (loss)/income |  |  |  |  | $ | (14.7 | ) |  |  |  |  |  | $ | 75.8 |
Ratios |  |  |  |  |  |  |  |  |  |  |
Loss ratio | 57.8 | % |  | 62.2 | % |  | 59.7 | % |  | 56.0 | % |  | 66.9 | % |  | 61.6 | %
Policy acquisition expense ratio | 21.7 | % |  | 10.0 | % |  | 16.5 | % |  | 19.6 | % |  | 14.8 | % |  | 17.1 | %
General and administrative expense ratio (4) | 9.7 | % |  | 24.8 | % |  | 21.2 | % |  | 14.9 | % |  | 22.7 | % |  | 21.3 | %
General and administrative expense ratio (excluding amortization and non-recurring expenses)(4) | 9.7 | % |  | 24.8 | % |  | 19.5 | % |  | 14.9 | % |  | 22.7 | % |  | 21.0 | %
Expense ratio | 31.4 | % |  | 34.8 | % |  | 37.7 | % |  | 34.5 | % |  | 37.5 | % |  | 38.4 | %
Expense ratio (excluding amortization and non-recurring expenses) | 31.4 | % |  | 34.8 | % |  | 36.0 | % |  | 34.5 | % |  | 37.5 | % |  | 38.1 | %
Combined ratio | 89.2 | % |  | 97.0 | % |  | 97.4 | % |  | 90.5 | % |  | 104.4 | % |  | 100.0 | %
Combined ratio (excluding amortization and non-recurring expenses) | 89.2 | % |  | 97.0 | % |  | 95.7 | % |  | 90.5 | % |  | 104.4 | % |  | 99.7 | %

(1) Amortization and non-recurring expenses includes $8.6 million of expenses related to the Operational Effectiveness and Efficiency Program.
(2) Other (expense)/income in the second quarter of 2018 and second quarter of 2017 included expense of $3.4 million and $3.3 million, respectively, related to a change in the fair value of loan notes issued by Silverton Re.
(3) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.
(4) The total group general and administrative expense ratio includes the impact from corporate and non-recurring expenses.
8

| ASPEN INSURANCE HOLDINGS LIMITED |  |
Consolidated Underwriting Results by Operating Segment |  |
|  |  | Six Months Ended June 30, 2018 |  | Six Months Ended June 30, 2017
(in US$ millions except for percentages) | Reinsurance |  | Insurance |  | Total |  | Reinsurance |  | Insurance |  | Total
Gross written premiums | $ | 949.5 |  |  | $ | 1,021.1 |  |  | $ | 1,970.6 |  |  | $ | 900.9 |  |  | $ | 919.2 |  |  | $ | 1,820.1 |
Net written premiums | 691.9 |  |  | 429.6 |  |  | 1,121.5 |  |  | 733.7 |  |  | 531.2 |  |  | 1,264.9 |
Gross earned premiums | 741.2 |  |  | 946.9 |  |  | 1,688.1 |  |  | 648.2 |  |  | 852.8 |  |  | 1,501.0 |
Net earned premiums | 571.5 |  |  | 481.5 |  |  | 1,053.0 |  |  | 550.2 |  |  | 592.9 |  |  | 1,143.1 |
Losses and loss adjustment expenses | 333.9 |  |  | 286.7 |  |  | 620.6 |  |  | 295.7 |  |  | 378.6 |  |  | 674.3 |
Amortization of deferred policy acquisition costs | 118.7 |  |  | 58.0 |  |  | 176.7 |  |  | 112.9 |  |  | 97.1 |  |  | 210.0 |
General and administrative expenses | 59.5 |  |  | 120.8 |  |  | 180.3 |  |  | 84.6 |  |  | 127.5 |  |  | 212.1 |
Underwriting income/(loss) | $ | 59.4 |  |  | $ | 16.0 |  |  | $ | 75.4 |  |  | $ | 57.0 |  |  | $ | (10.3 | ) |  | $ | 46.7 |
Net investment income |  |  |  |  | 97.7 |  |  |  |  |  |  | 95.1 |
Net realized and unrealized investment (losses)/gains |  |  |  |  | (58.4 | ) |  |  |  |  |  | 88.2 |
Realized (loss) on debt extinguishment |  |  |  |  | (8.6 | ) |  |  |  |  |  | — |
Corporate expenses |  |  |  |  | (29.7 | ) |  |  |  |  |  | (24.8 | )
Amortization and non-recurring expenses (1) |  |  |  |  | (21.2 | ) |  |  |  |  |  | (4.3 | )
Other income/(expense)(2) |  |  |  |  | 0.1 |  |  |  |  |  |  | (1.0 | )
Interest expense |  |  |  |  | (15.0 | ) |  |  |  |  |  | (14.8 | )
Net realized and unrealized foreign exchange (losses) (3) |  |  |  |  | (22.1 | ) |  |  |  |  |  | (8.8 | )
Income before tax |  |  |  |  | $ | 18.2 |  |  |  |  |  |  | $ | 176.3 |
Income tax (expense) |  |  |  |  | (2.1 | ) |  |  |  |  |  | (4.0 | )
Net income |  |  |  |  | $ | 16.1 |  |  |  |  |  |  | $ | 172.3 |
Ratios |  |  |  |  |  |  |  |  |  |  |
Loss ratio | 58.4 | % |  | 59.5 | % |  | 58.9 | % |  | 53.7 | % |  | 63.9 | % |  | 59.0 | %
Policy acquisition expense ratio | 20.8 | % |  | 12.0 | % |  | 16.8 | % |  | 20.5 | % |  | 16.4 | % |  | 18.4 | %
General and administrative expense ratio (4) | 10.4 | % |  | 25.1 | % |  | 22.0 | % |  | 15.4 | % |  | 21.5 | % |  | 21.1 | %
General and administrative expense ratio (excluding amortization and non-recurring expenses)(5) | 10.4 | % |  | 25.1 | % |  | 19.9 | % |  | 15.4 | % |  | 21.5 | % |  | 20.7 | %
Expense ratio | 31.2 | % |  | 37.1 | % |  | 38.8 | % |  | 35.9 | % |  | 37.9 | % |  | 39.5 | %
Expense ratio (excluding amortization and non-recurring expenses) | 31.2 | % |  | 37.1 | % |  | 36.7 | % |  | 35.9 | % |  | 37.9 | % |  | 39.1 | %
Combined ratio | 89.6 | % |  | 96.6 | % |  | 97.7 | % |  | 89.6 | % |  | 101.8 | % |  | 98.5 | %
Combined ratio (excluding amortization and non-recurring expenses) | 89.6 | % |  | 96.6 | % |  | 95.6 | % |  | 89.6 | % |  | 101.8 | % |  | 98.1 | %

(1) Amortization and non-recurring expenses includes $20.4 million of expenses related to the Operational Effectiveness and Efficiency Program.
(2) Other income/(expense) in the first half of 2018 and the first half of 2017 included expense of $2.4 million and $6.2 million, respectively, related to a change in the fair value of loan notes issued by Silverton Re.
(3) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.
(4) The total group general and administrative expense ratio includes the impact from corporate and non-recurring expenses.
9

| ASPEN INSURANCE HOLDINGS LIMITED
Reinsurance Segment - Quarterly Results
(in US$ millions except for percentages) |  | Q2 2018 |  | Q1 2018 |  | Q4 2017 |  | Q3 2017 |  | Q2 2017 |  | Q1 2017 |
Gross written premiums |  | $ | 326.0 |  |  | $ | 623.5 |  |  | $ | 216.1 |  |  | $ | 431.5 |  |  | $ | 335.6 |  |  | $ | 565.3 |  |
Net written premiums |  | 266.9 |  |  | 425.0 |  |  | 152.7 |  |  | 363.6 |  |  | 285.5 |  |  | 448.2 |  |
Gross earned premiums |  | 366.2 |  |  | 375.0 |  |  | 339.6 |  |  | 464.0 |  |  | 320.6 |  |  | 327.6 |  |
Net earned premiums |  | 289.0 |  |  | 282.5 |  |  | 273.9 |  |  | 382.0 |  |  | 272.7 |  |  | 277.5 |  |
Net losses and loss adjustment expenses |  | 167.0 |  |  | 166.9 |  |  | 318.5 |  |  | 502.2 |  |  | 152.6 |  |  | 143.1 |  |
Amortization of deferred policy acquisition costs |  | 62.8 |  |  | 55.9 |  |  | 61.1 |  |  | 61.5 |  |  | 53.4 |  |  | 59.5 |  |
General and administrative expenses |  | 27.9 |  |  | 31.6 |  |  | 39.9 |  |  | 32.8 |  |  | 40.7 |  |  | 43.9 |  |
Underwriting income/(loss) |  | $ | 31.3 |  |  | $ | 28.1 |  |  | $ | (145.6 | ) |  | $ | (214.5 | ) |  | $ | 26.0 |  |  | $ | 31.0 |  |
Ratios |  |  |  |  |  |  |  |  |  |  |  |  |
Loss ratio |  | 57.8 | % |  | 59.1 | % |  | 116.3 | % |  | 131.5 | % |  | 56.0 | % |  | 51.6 | % |
Policy acquisition expense ratio |  | 21.7 | % |  | 19.8 | % |  | 22.3 | % |  | 16.1 | % |  | 19.6 | % |  | 21.4 | % |
General and administrative expense ratio |  | 9.7 | % |  | 11.2 | % |  | 14.6 | % |  | 8.6 | % |  | 14.9 | % |  | 15.8 | % |
Expense ratio |  | 31.4 | % |  | 31.0 | % |  | 36.9 | % |  | 24.7 | % |  | 34.5 | % |  | 37.2 | % |
Combined ratio |  | 89.2 | % |  | 90.1 | % |  | 153.2 | % |  | 156.2 | % |  | 90.5 | % |  | 88.8 | % |
Accident Year Ex-cat Loss Ratio |  |  |  |  |  |  |  |  |  |  |  |  |
Loss ratio |  | 57.8 | % |  | 59.1 | % |  | 116.3 | % |  | 131.5 | % |  | 56.0 | % |  | 51.6 | % |
Prior year loss development |  | 10.9 | % |  | 2.7 | % |  | 4.0 | % |  | 4.8 | % |  | 12.0 | % |  | 7.6 | % |
Catastrophe losses |  | (3.5 | )% |  | (5.2 | )% |  | (49.6 | )% |  | (74.6 | )% |  | (3.8 | )% |  | (8.9 | )% |
Accident year ex-cat loss ratio |  | 65.2 | % |  | 56.6 | % |  | 70.7 | % |  | 61.7 | % |  | 64.2 | % |  | 50.3 | % |

10

| ASPEN INSURANCE HOLDINGS LIMITED
Insurance Segment - Quarterly Results
(in US$ millions except for percentages) |  | Q2 2018 |  | Q1 2018 |  | Q4 2017 |  | Q3 2017 |  | Q2 2017 |  | Q1 2017 |
Gross written premiums |  | $ | 527.8 |  |  | $ | 493.3 |  |  | $ | 472.2 |  |  | $ | 421.0 |  |  | $ | 486.5 |  |  | $ | 432.7 |  |
Net written premiums |  | 219.1 |  |  | 210.5 |  |  | 187.5 |  |  | 243.8 |  |  | 293.2 |  |  | 238.0 |  |
Gross earned premiums |  | 479.3 |  |  | 467.6 |  |  | 455.3 |  |  | 449.3 |  |  | 429.1 |  |  | 423.7 |  |
Net earned premiums |  | 230.5 |  |  | 251.0 |  |  | 237.1 |  |  | 270.5 |  |  | 289.3 |  |  | 303.6 |  |
Net losses and loss adjustment expenses |  | 143.4 |  |  | 143.3 |  |  | 225.7 |  |  | 274.0 |  |  | 193.5 |  |  | 185.1 |  |
Amortization of deferred policy acquisition costs |  | 23.1 |  |  | 34.9 |  |  | 24.0 |  |  | 43.9 |  |  | 42.9 |  |  | 54.2 |  |
General and administrative expenses |  | 57.2 |  |  | 63.6 |  |  | 67.0 |  |  | 59.4 |  |  | 65.7 |  |  | 61.8 |  |
Underwriting income/(loss) |  | $ | 6.8 |  |  | $ | 9.2 |  |  | $ | (79.6 | ) |  | $ | (106.8 | ) |  | $ | (12.8 | ) |  | $ | 2.5 |  |
Ratios |  |  |  |  |  |  |  |  |  |  |  |  |
Loss ratio |  | 62.2 | % |  | 57.1 | % |  | 95.2 | % |  | 101.3 | % |  | 66.9 | % |  | 61.0 | % |
Policy acquisition expense ratio |  | 10.0 | % |  | 13.9 | % |  | 10.1 | % |  | 16.2 | % |  | 14.8 | % |  | 17.9 | % |
General and administrative expense ratio |  | 24.8 | % |  | 25.3 | % |  | 28.3 | % |  | 22.0 | % |  | 22.7 | % |  | 20.4 | % |
Expense ratio |  | 34.8 | % |  | 39.2 | % |  | 38.4 | % |  | 38.2 | % |  | 37.5 | % |  | 38.3 | % |
Combined ratio |  | 97.0 | % |  | 96.3 | % |  | 133.6 | % |  | 139.5 | % |  | 104.4 | % |  | 99.3 | % |
Accident Year Ex-cat Loss Ratio |  |  |  |  |  |  |  |  |  |  |  |  |
Loss ratio |  | 62.2 | % |  | 57.1 | % |  | 95.2 | % |  | 101.3 | % |  | 66.9 | % |  | 61.0 | % |
Prior year loss development |  | 4.8 | % |  | 12.0 | % |  | 0.8 | % |  | 0.3 | % |  | 5.6 | % |  | 1.6 | % |
Catastrophe losses |  | (3.5 | )% |  | (3.7 | )% |  | (1.0 | )% |  | (30.3 | )% |  | (9.4 | )% |  | (1.5 | )% |
Accident year ex-cat loss ratio |  | 63.5 | % |  | 65.4 | % |  | 95.0 | % |  | 71.3 | % |  | 63.1 | % |  | 61.1 | % |

11

| ASPEN INSURANCE HOLDINGS LIMITED |
Written and Earned Premiums by Segment and Lines of Business |
(in US$ millions) |  |  |  |  |  |  |  |  |  |  |  |  |
Gross Written Premiums |  | Q2 2018 |  | Q1 2018 |  | Q4 2017 |  | Q3 2017 |  | Q2 2017 |  | Q1 2017 |
| Reinsurance |  |  |  |  |  |  |  |  |  |  |  |  |
| Property Catastrophe Reinsurance |  | $ | 77.2 |  |  | $ | 151.2 |  |  | $ | 12.9 |  |  | $ | 63.3 |  |  | $ | 72.4 |  |  | $ | 130.7 |  |
| Other Property Reinsurance |  | 86.6 |  |  | 104.8 |  |  | 63.6 |  |  | 88.1 |  |  | 79.7 |  |  | 118.9 |  |
| Casualty Reinsurance |  | 58.4 |  |  | 143.3 |  |  | 46.4 |  |  | 75.8 |  |  | 53.1 |  |  | 143.7 |  |
| Specialty Reinsurance |  | 103.8 |  |  | 224.2 |  |  | 93.2 |  |  | 204.3 |  |  | 130.4 |  |  | 172.0 |  |
| Total Reinsurance |  | $ | 326.0 |  |  | $ | 623.5 |  |  | $ | 216.1 |  |  | $ | 431.5 |  |  | $ | 335.6 |  |  | $ | 565.3 |  |
| Insurance |  |  |  |  |  |  |  |  |  |  |  |  |
| Property and Casualty Insurance |  | $ | 263.2 |  |  | $ | 231.3 |  |  | $ | 201.9 |  |  | $ | 194.6 |  |  | $ | 249.3 |  |  | $ | 211.1 |  |
| Marine, Aviation and Energy Insurance |  | 109.6 |  |  | 101.5 |  |  | 100.8 |  |  | 86.0 |  |  | 92.7 |  |  | 105.8 |  |
| Financial and Professional Lines Insurance |  | 155.0 |  |  | 160.5 |  |  | 169.5 |  |  | 140.4 |  |  | 144.5 |  |  | 115.8 |  |
| Total Insurance |  | $ | 527.8 |  |  | $ | 493.3 |  |  | $ | 472.2 |  |  | $ | 421.0 |  |  | $ | 486.5 |  |  | $ | 432.7 |  |
| Total Gross Written Premiums |  | $ | 853.8 |  |  | $ | 1,116.8 |  |  | $ | 688.3 |  |  | $ | 852.5 |  |  | $ | 822.1 |  |  | $ | 998.0 |  |
Net Written Premiums |  |  |  |  |  |  |  |  |  |  |  |  |
| Reinsurance |  |  |  |  |  |  |  |  |  |  |  |  |
| Property Catastrophe Reinsurance |  | $ | 40.9 |  |  | $ | 54.1 |  |  | $ | 3.0 |  |  | $ | 40.3 |  |  | $ | 58.2 |  |  | $ | 71.1 |  |
| Other Property Reinsurance |  | 71.7 |  |  | 77.4 |  |  | 55.1 |  |  | 76.0 |  |  | 65.6 |  |  | 89.0 |  |
| Casualty Reinsurance |  | 54.3 |  |  | 136.7 |  |  | 42.9 |  |  | 72.9 |  |  | 46.5 |  |  | 142.0 |  |
| Specialty Reinsurance |  | 100.0 |  |  | 156.8 |  |  | 51.7 |  |  | 174.4 |  |  | 115.2 |  |  | 146.1 |  |
| Total Reinsurance |  | $ | 266.9 |  |  | $ | 425.0 |  |  | $ | 152.7 |  |  | $ | 363.6 |  |  | $ | 285.5 |  |  | $ | 448.2 |  |
| Insurance |  |  |  |  |  |  |  |  |  |  |  |  |
| Property and Casualty Insurance |  | $ | 91.4 |  |  | $ | 63.7 |  |  | $ | 41.4 |  |  | $ | 122.7 |  |  | $ | 180.0 |  |  | $ | 94.8 |  |
| Marine, Aviation and Energy Insurance |  | 44.4 |  |  | 82.0 |  |  | 53.2 |  |  | 50.7 |  |  | 40.8 |  |  | 71.1 |  |
| Financial and Professional Lines Insurance |  | 83.3 |  |  | 64.8 |  |  | 92.9 |  |  | 70.4 |  |  | 72.4 |  |  | 72.1 |  |
| Total Insurance |  | $ | 219.1 |  |  | $ | 210.5 |  |  | $ | 187.5 |  |  | $ | 243.8 |  |  | $ | 293.2 |  |  | $ | 238.0 |  |
| Total Net Written Premiums |  | $ | 486.0 |  |  | $ | 635.5 |  |  | $ | 340.2 |  |  | $ | 607.4 |  |  | $ | 578.7 |  |  | $ | 686.2 |  |
Net Earned Premiums |  |  |  |  |  |  |  |  |  |  |  |  |
| Reinsurance |  |  |  |  |  |  |  |  |  |  |  |  |
| Property Catastrophe Reinsurance |  | $ | 36.9 |  |  | $ | 29.4 |  |  | $ | 45.2 |  |  | $ | 51.3 |  |  | $ | 48.3 |  |  | $ | 34.0 |  |
| Other Property Reinsurance |  | 76.9 |  |  | 69.3 |  |  | 72.6 |  |  | 76.8 |  |  | 66.2 |  |  | 77.3 |  |
| Casualty Reinsurance |  | 80.5 |  |  | 81.2 |  |  | 67.5 |  |  | 74.1 |  |  | 68.9 |  |  | 81.8 |  |
| Specialty Reinsurance |  | 94.7 |  |  | 102.6 |  |  | 88.6 |  |  | 179.8 |  |  | 89.3 |  |  | 84.4 |  |
| Total Reinsurance |  | $ | 289.0 |  |  | $ | 282.5 |  |  | $ | 273.9 |  |  | $ | 382.0 |  |  | $ | 272.7 |  |  | $ | 277.5 |  |
| Insurance |  |  |  |  |  |  |  |  |  |  |  |  |
| Property and Casualty Insurance |  | $ | 91.5 |  |  | $ | 108.7 |  |  | $ | 106.7 |  |  | $ | 137.7 |  |  | $ | 156.7 |  |  | $ | 144.4 |  |
| Marine, Aviation and Energy Insurance |  | 61.6 |  |  | 64.5 |  |  | 59.9 |  |  | 53.8 |  |  | 52.7 |  |  | 77.4 |  |
| Financial and Professional Lines Insurance |  | 77.4 |  |  | 77.8 |  |  | 70.5 |  |  | 79.0 |  |  | 79.9 |  |  | 81.8 |  |
| Total Insurance |  | $ | 230.5 |  |  | $ | 251.0 |  |  | $ | 237.1 |  |  | $ | 270.5 |  |  | $ | 289.3 |  |  | $ | 303.6 |  |
| Total Net Earned Premiums |  | $ | 519.5 |  |  | $ | 533.5 |  |  | $ | 511.0 |  |  | $ | 652.5 |  |  | $ | 562.0 |  |  | $ | 581.1 |  |

12

| ASPEN INSURANCE HOLDINGS LIMITED |
Consolidated Statements of Changes in Shareholders' Equity |
|  | Six Months Ended June 30,
(in US$ millions) |  | 2018 |  | 2017
Ordinary shares |  |  |  |
| Beginning and end of period |  | $ | 0.1 |  |  | $ | 0.1 |
Preference shares |  |  |  |
| Beginning and end of period |  | — |  |  | — |
Non-controlling interest |  |  |  |
| Beginning of period |  | 2.7 |  |  | 1.4 |
| Net change for the period |  | 0.3 |  |  | 0.2 |
| End of period |  | 3.0 |  |  | 1.6 |
Additional paid-in capital |  |  |  |
| Beginning of period |  | 954.7 |  |  | 1,259.6 |
| New shares issued |  | 2.5 |  |  | 0.4 |
| Ordinary shares repurchased |  | — |  |  | (10.0 | )
| Preference shares redemption |  | — |  |  | (133.2 | )
| Preference share redemption costs |  | — |  |  | 2.4 |
| Share-based compensation |  | 8.2 |  |  | 6.0 |
| End of period |  | 965.4 |  |  | 1,125.2 |
Retained earnings |  |  |  |
| Beginning of period |  | 2,026.9 |  |  | 2,392.3 |
| Net income for the period |  | 16.1 |  |  | 172.3 |
| Dividends paid on ordinary and preference shares |  | (43.8 | ) |  | (48.6 | )
| Preference shares redemption costs |  | — |  |  | (2.4 | )
| Proportion due to non-controlling interest |  | (0.3 | ) |  | (0.2 | )
| Share-based payment |  | — |  |  | 2.8 |
| End of period |  | 1,998.9 |  |  | 2,516.2 |
Accumulated other comprehensive income: |  |  |  |
Cumulative foreign currency translation adjustments, net of taxes: |  |  |  |
| Beginning of period |  | (67.7 | ) |  | (27.1 | )
| Change for the period |  | 16.9 |  |  | (34.2 | )
| End of period |  | (50.8 | ) |  | (61.3 | )
Gain on derivatives: |  |  |  |
| Beginning of period |  | 2.1 |  |  | (0.5 | )
| Net change from current period hedged transactions |  | (1.4 | ) |  | 3.2 |
| End of period |  | 0.7 |  |  | 2.7 |
Unrealized appreciation on available for sale investments, net of taxes: |  |  |
| Beginning of period |  | 9.7 |  |  | 22.5 |
| Change for the period |  | (99.0 | ) |  | 13.9 |
| End of period |  | (89.3 | ) |  | 36.4 |
Total accumulated other comprehensive (loss) |  | (139.4 | ) |  | (22.2 | )
Total shareholders' equity |  | $ | 2,828.0 |  |  | $ | 3,620.9 |

13

| ASPEN INSURANCE HOLDINGS LIMITED |  |  |  |
Consolidated Statements of Comprehensive Income |  |  |  |
|  |  |  | Three Months Ended June 30, |  | Six Months Ended June 30,
(in US$ millions) |  | 2018 |  | 2017 |  | 2018 |  | 2017
Net (loss)/income adjusted for non-controlling interest |  | $ | (14.8 | ) |  | $ | 75.7 |  |  | $ | 15.8 |  |  | $ | 172.1 |
Other comprehensive income, net of taxes: |  |  |  |  |  |  |  |
| Available for sale investments: |  |  |  |  |  |  |  |
| Reclassification adjustment for net realized (gains)/losses included in net income |  | 2.9 |  |  | (0.8 | ) |  | 2.9 |  |  | (1.6 | )
| Change in net unrealized gains on available for sale securities held |  | (24.5 | ) |  | 12.6 |  |  | (101.9 | ) |  | 15.5 |
| Net change from current period hedged transactions |  | (2.1 | ) |  | 2.0 |  |  | (1.4 | ) |  | 3.2 |
| Change in foreign currency translation adjustment |  | 23.4 |  |  | (21.3 | ) |  | 16.9 |  |  | (34.2 | )
| Other comprehensive (loss) |  | (0.3 | ) |  | (7.5 | ) |  | (83.5 | ) |  | (17.1 | )
Comprehensive (loss)/income |  | $ | (15.1 | ) |  | $ | 68.2 |  |  | $ | (67.7 | ) |  | $ | 155.0 |

14

| ASPEN INSURANCE HOLDINGS LIMITED |  |  |  |
Condensed Consolidated Statements of Cash Flows |  |  |  |
|  |  |  | Three Months Ended June 30, |  | Six Months Ended June 30,
(in US$ millions) |  | 2018 |  | 2017 |  | 2018 |  | 2017
Net cash (used in) operating activities |  | $ | (88.6 | ) |  | $ | (20.2 | ) |  | $ | (211.4 | ) |  | $ | (104.5 | )
Net cash from investing activities |  | 77.0 |  |  | 409.7 |  |  | 462.3 |  |  | 365.6 |
Net cash (used in) financing activities |  | (171.3 | ) |  | (38.8 | ) |  | (243.0 | ) |  | (314.6 | )
Effect of exchange rate movements on cash and cash equivalents |  | 6.7 |  |  | 4.6 |  |  | 8.0 |  |  | 8.1 |
(Decrease)/increase in cash and cash equivalents |  | (176.2 | ) |  | 355.3 |  |  | 15.9 |  |  | (45.4 | )
Cash at beginning of period |  | 1,246.9 |  |  | 873.1 |  |  | 1,054.8 |  |  | 1,273.8 |
Cash at end of period |  | $ | 1,070.7 |  |  | $ | 1,228.4 |  |  | $ | 1,070.7 |  |  | $ | 1,228.4 |

15

| ASPEN INSURANCE HOLDINGS LIMITED
Reserves for Losses and Loss Adjustment Expenses
(in US$ millions) | For the Six Months Ended June 30, 2018 |  | For the Six Months Ended June 30, 2017 |  | For the Twelve Months Ended December 31, 2017
Provision for losses and loss adjustment expenses at the start of the period | $ | 6,749.5 |  |  | 5,319.9 |  |  | $ | 5,319.9 |
Reinsurance recoverables | (1,515.2 | ) |  | (560.7 | ) |  | (560.7 | )
Net loss and loss adjustment expenses at the start of the period | 5,234.3 |  |  | 4,759.2 |  |  | 4,759.2 |
Net loss and loss adjustment expenses assumed | — |  |  | — |  |  | (125.5 | )
Provision for losses and loss adjustment expenses for claims incurred |  |  |  |  |
Current period | 700.8 |  |  | 749.2 |  |  | 2,100.1 |
Prior period release | (80.2 | ) |  | (74.9 | ) |  | (105.4 | )
Total incurred | 620.6 |  |  | 674.3 |  |  | 1,994.7 |
Losses and loss adjustment expenses payments for claims incurred | (924.4 | ) |  | (741.1 | ) |  | (1,555.1 | )
Foreign exchange losses | (54.1 | ) |  | 99.6 |  |  | 161.0 |
Net loss and loss adjustment expenses reserves at the end of the period | 4,876.4 |  |  | 4,792.0 |  |  | 5,234.3 |
Reinsurance recoverables on unpaid losses at the end of the period | 1,656.4 |  |  | 779.4 |  |  | 1,515.2 |
Gross loss and loss adjustment expenses reserves at the end of the period | $ | 6,532.8 |  |  | 5,571.4 |  |  | $ | 6,749.5 |

16

| ASPEN INSURANCE HOLDINGS LIMITED |  |
Reserves by Operating Segment |  |
|  |  | As at June 30, 2018 |  | As at December 31, 2017
(in US$ millions) | Gross |  | Reinsurance Recoverables |  | Net |  | Gross |  | Reinsurance Recoverables |  | Net
Reinsurance | $ | 3,017.7 |  |  | $ | (273.6 | ) |  | $ | 2,744.1 |  |  | $ | 3,186.4 |  |  | $ | (269.3 | ) |  | $ | 2,917.1 |
Insurance | 3,515.1 |  |  | (1,382.8 | ) |  | 2,132.3 |  |  | 3,563.1 |  |  | (1,245.9 | ) |  | 2,317.2 |
Total losses and loss adjustment expense reserves | $ | 6,532.8 |  |  | $ | (1,656.4 | ) |  | $ | 4,876.4 |  |  | $ | 6,749.5 |  |  | $ | (1,515.2 | ) |  | $ | 5,234.3 |

17

| ASPEN INSURANCE HOLDINGS LIMITED
Prior Year Reserve Movements
(in US$ millions) | Three Months Ended June 30, 2018 |  | Three Months Ended June 30, 2017
|  |  | Gross |  | Reinsurance Recoverables |  | Net |  | Gross |  | Reinsurance Recoverables |  | Net
Reinsurance | $ | 52.6 |  |  | $ | (21.1 | ) |  | $ | 31.5 |  |  | $ | 20.8 |  |  | $ | 11.8 |  |  | $ | 32.6 |
Insurance | (52.8 | ) |  | 63.8 |  |  | 11.0 |  |  | (10.9 | ) |  | 27.0 |  |  | 16.1 |
Movements in reserves for prior years during the period | $ | (0.2 | ) |  | $ | 42.7 |  |  | $ | 42.5 |  |  | $ | 9.9 |  |  | $ | 38.8 |  |  | $ | 48.7 |
|  |  | Six Months Ended June 30, 2018 |  | Six Months Ended June 30, 2017
|  |  | Gross |  | Reinsurance Recoverables |  | Net |  | Gross |  | Reinsurance Recoverables |  | Net
Reinsurance | $ | 55.5 |  |  | $ | (16.6 | ) |  | $ | 38.9 |  |  | $ | 44.8 |  |  | $ | 9.0 |  |  | $ | 53.8 |
Insurance | (13.0 | ) |  | 54.3 |  |  | 41.3 |  |  | (14.7 | ) |  | 35.8 |  |  | 21.1 |
Movements in reserves for prior years during the period | $ | 42.5 |  |  | $ | 37.7 |  |  | $ | 80.2 |  |  | $ | 30.1 |  |  | $ | 44.8 |  |  | $ | 74.9 |

18

| ASPEN INSURANCE HOLDINGS LIMITED |
Consolidated Investment Portfolio |
(in US$ millions) |  | Fair Market Value
|  | June 30, 2018 |  | March 31, 2018 |  | December 31, 2017 |  | September 30, 2017 |  | June 30, 2017 |  | March 31, 2017 |
Marketable Securities - Available For Sale |  |  |  |  |  |  |  |  |  |  |  |  |
U.S. government securities |  | $ | 1,229.6 |  |  | $ | 1,292.2 |  |  | $ | 1,159.4 |  |  | $ | 1,172.7 |  |  | $ | 1,220.8 |  |  | $ | 1,267.1 |  |
U.S. agency securities |  | 46.6 |  |  | 52.7 |  |  | 52.1 |  |  | 62.1 |  |  | 75.5 |  |  | 107.4 |  |
Municipal securities |  | 105.7 |  |  | 47.6 |  |  | 54.9 |  |  | 50.1 |  |  | 32.8 |  |  | 24.4 |  |
Corporate securities |  | 2,267.2 |  |  | 2,446.2 |  |  | 2,415.7 |  |  | 2,468.3 |  |  | 2,503.4 |  |  | 2,587.7 |  |
Non-U.S. government securities |  | 430.2 |  |  | 483.4 |  |  | 484.9 |  |  | 531.7 |  |  | 525.9 |  |  | 494.2 |  |
Asset-backed securities |  | 18.4 |  |  | 18.5 |  |  | 26.2 |  |  | 33.7 |  |  | 48.9 |  |  | 54.8 |  |
Non-U.S. government-backed corporate securities |  | 91.8 |  |  | 97.8 |  |  | 91.3 |  |  | 94.0 |  |  | 92.6 |  |  | 84.5 |  |
Mortgage-backed securities |  | 890.5 |  |  | 973.8 |  |  | 946.5 |  |  | 952.8 |  |  | 997.4 |  |  | 1,044.3 |  |
Total fixed income securities |  | 5,080.0 |  |  | 5,412.2 |  |  | 5,231.0 |  |  | 5,365.4 |  |  | 5,497.3 |  |  | 5,664.4 |  |
Short-term investments |  | 72.2 |  |  | 54.6 |  |  | 89.9 |  |  | 34.4 |  |  | 41.9 |  |  | 163.5 |  |
Total Available For Sale |  | $ | 5,152.2 |  |  | $ | 5,466.8 |  |  | $ | 5,320.9 |  |  | $ | 5,399.8 |  |  | $ | 5,539.2 |  |  | $ | 5,827.9 |  |
Marketable Securities - Trading |  |  |  |  |  |  |  |  |  |  |  |  |
U.S. government securities |  | $ | 155.3 |  |  | $ | 141.7 |  |  | $ | 161.9 |  |  | $ | 160.6 |  |  | $ | 112.8 |  |  | $ | 95.4 |  |
Municipal securities |  | 77.8 |  |  | 74.3 |  |  | 32.2 |  |  | 32.3 |  |  | 5.7 |  |  | 15.6 |  |
Corporate securities |  | 968.6 |  |  | 1,003.6 |  |  | 1,046.3 |  |  | 1,045.0 |  |  | 896.0 |  |  | 866.2 |  |
Non-U.S. government securities |  | 219.3 |  |  | 216.6 |  |  | 202.5 |  |  | 210.9 |  |  | 186.5 |  |  | 191.7 |  |
Asset-backed securities |  | 7.2 |  |  | 8.3 |  |  | 9.9 |  |  | 11.1 |  |  | 12.2 |  |  | 13.4 |  |
Mortgage-backed securities |  | 187.7 |  |  | 192.1 |  |  | 195.5 |  |  | 203.1 |  |  | 142.3 |  |  | 130.9 |  |
Non-U.S. government-backed corporate securities |  | — |  |  | 1.0 |  |  | 1.0 |  |  | 2.0 |  |  | 2.0 |  |  | — |  |
Total fixed income securities |  | 1,615.9 |  |  | 1,637.6 |  |  | 1,649.3 |  |  | 1,665.0 |  |  | 1,357.5 |  |  | 1,313.2 |  |
Short-term investments |  | 27.4 |  |  | 27.0 |  |  | 73.0 |  |  | 90.4 |  |  | 73.7 |  |  | 184.6 |  |
Equity securities |  | — |  |  | — |  |  | 491.0 |  |  | 468.5 |  |  | 658.7 |  |  | 623.6 |  |
Catastrophe bonds |  | 35.5 |  |  | 34.8 |  |  | 32.4 |  |  | 30.3 |  |  | 28.3 |  |  | 41.8 |  |
Total Trading |  | $ | 1,678.8 |  |  | $ | 1,699.4 |  |  | $ | 2,245.7 |  |  | $ | 2,254.2 |  |  | $ | 2,118.2 |  |  | $ | 2,163.2 |  |
Other Investments |  | $ | 153.3 |  |  | $ | 66.1 |  |  | $ | 66.4 |  |  | $ | 4.0 |  |  | $ | 3.9 |  |  | $ | 5.0 |  |
Cash |  | 1,070.7 |  |  | 1,246.9 |  |  | 1,054.8 |  |  | 1,209.3 |  |  | 1,228.4 |  |  | 873.1 |  |
Accrued interest |  | 45.2 |  |  | 44.3 |  |  | 45.2 |  |  | 45.3 |  |  | 46.9 |  |  | 46.5 |  |
| Total Cash and Accrued Interest |  | $ | 1,115.9 |  |  | $ | 1,291.2 |  |  | $ | 1,100.0 |  |  | $ | 1,254.6 |  |  | $ | 1,275.3 |  |  | $ | 919.6 |  |
| Total Cash and Investments |  | $ | 8,100.2 |  |  | $ | 8,523.5 |  |  | $ | 8,733.0 |  |  | $ | 8,912.6 |  |  | $ | 8,936.6 |  |  | $ | 8,915.7 |  |

19

| ASPEN INSURANCE HOLDINGS LIMITED |
Investment Analysis |
(in US$ millions except for percentages) | Q2 2018 |  | Q1 2018 |  | Q4 2017 |  | Q3 2017 |  | Q2 2017 |  | Q1 2017 |
Net investment income from fixed income investments and cash | $ | 49.7 |  |  | $ | 46.1 |  |  | $ | 45.6 |  |  | $ | 43.6 |  |  | $ | 43.7 |  |  | $ | 42.5 |  |
Net investment income from equity securities | 0.7 |  |  | 1.2 |  |  | 1.9 |  |  | 2.8 |  |  | 3.7 |  |  | 5.2 |  |
Net investment income | 50.4 |  |  | 47.3 |  |  | 47.5 |  |  | 46.4 |  |  | 47.4 |  |  | 47.7 |  |
Net realized and unrealized investment (losses)/gains | (20.7 | ) |  | (37.7 | ) |  | 15.0 |  |  | 17.6 |  |  | 42.1 |  |  | 46.5 |  |
Other-than-temporary impairment charges | — |  |  | — |  |  | (0.2 | ) |  | (0.1 | ) |  | (0.1 | ) |  | (0.3 | ) |
Net realized and unrealized investment (losses)/gains | (20.7 | ) |  | (37.7 | ) |  | 14.8 |  |  | 17.5 |  |  | 42.0 |  |  | 46.2 |  |
Change in unrealized (losses)/gains on available for sale investments (gross of tax) | (22.9 | ) |  | (82.8 | ) |  | (30.0 | ) |  | 0.3 |  |  | 12.9 |  |  | 2.0 |  |
Total return/(loss) on investments | $ | 6.8 |  |  | $ | (73.2 | ) |  | $ | 32.3 |  |  | $ | 64.2 |  |  | $ | 102.3 |  |  | $ | 95.9 |  |
Portfolio Characteristics |  |  |  |  |  |  |  |  |  |  |  |
Fixed income portfolio book yield | 2.63 | % |  | 2.63 | % |  | 2.56 | % |  | 2.54 | % |  | 2.53 | % |  | 2.53 | % |
Fixed income portfolio duration | 3.9 years |  | 4 years |  | 3.9 years |  | 3.9 years |  | 3.9 years |  | 3.9 years |

20

| ASPEN INSURANCE HOLDINGS LIMITED |
Book Value Per Ordinary Share |
(in US$ millions except for number of shares and per share amounts) |  | June 30, 2018 |  | March 31, 2018 |  | December 31, 2017 |  | September 30, 2017 |  | June 30, 2017 |  | March 31, 2017 |
Net assets |  | $ | 2,828.0 |  |  | $ | 2,859.0 |  |  | $ | 2,928.5 |  |  | $ | 3,162.9 |  |  | $ | 3,620.9 |  |  | $ | 3,594.4 |  |
Less: Preference shares |  | (511.9 | ) |  | (511.9 | ) |  | (511.9 | ) |  | (511.9 | ) |  | (666.3 | ) |  | (666.3 | ) |
Less: Non-controlling interest |  |  | (3.0 | ) |  | (2.9 | ) |  | (2.7 | ) |  | (2.2 | ) |  | (1.6 | ) |  | (1.5 | ) |
Total |  |  |  | $ | 2,313.1 |  |  | $ | 2,344.2 |  |  | $ | 2,413.9 |  |  | $ | 2,648.8 |  |  | $ | 2,953.0 |  |  | $ | 2,926.6 |  |
Ordinary shares outstanding (in millions) |  | 59.688 |  |  | 59.653 |  |  | 59.474 |  |  | 59.407 |  |  | 59.844 |  |  | 59.988 |  |
Ordinary shares and dilutive potential ordinary shares (in millions) |  | 60.534 |  |  | 60.574 |  |  | 60.202 |  |  | 60.200 |  |  | 60.712 |  |  | 61.107 |  |
Book value per ordinary share |  | $ | 38.75 |  |  | $ | 39.30 |  |  | $ | 40.59 |  |  | $ | 44.59 |  |  | $ | 49.34 |  |  | $ | 48.79 |  |
Diluted book value per ordinary share |  | $ | 38.21 |  |  | $ | 38.70 |  |  | $ | 40.10 |  |  | $ | 44.00 |  |  | $ | 48.64 |  |  | $ | 47.89 |  |
The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. |

21

| ASPEN INSURANCE HOLDINGS LIMITED |  |  |  |
Operating Income Reconciliation |  |  |  |
Net income is adjusted to exclude after-tax change in net foreign exchange gains and losses, realized gains and losses in investments and non-recurring items. |  |  |  |
|  | Three Months Ended |  | Six Months Ended
(in US$ millions except where stated) |  | June 30, 2018 |  | June 30, 2017 |  | June 30, 2018 |  | June 30, 2017
Net (loss)/income as reported |  | $ | (14.7 | ) |  | $ | 75.8 |  |  | $ | 16.1 |  |  | $ | 172.3 |
Preference share redemption costs |  | — |  |  | — |  |  | — |  |  | (2.4 | )
Net change attributable to non-controlling interest |  | (0.1 | ) |  | (0.1 | ) |  | (0.3 | ) |  | (0.2 | )
Preference share dividends |  | (7.6 | ) |  | (10.5 | ) |  | (15.2 | ) |  | (21.0 | )
Net (loss)/income available to ordinary shareholders |  | (22.4 | ) |  | 65.2 |  |  | 0.6 |  |  | 148.7 |
Add (deduct) after tax income: |  |  |  |  |  |  |  |
| Net foreign exchange losses |  | 32.6 |  |  | 3.0 |  |  | 17.2 |  |  | 8.1 |
| Net realized losses/(gains) on investments |  | 20.3 |  |  | (41.4 | ) |  | 58.1 |  |  | (85.2 | )
| Net realized loss on debt extinguishment |  | 8.6 |  |  | — |  |  | 8.6 |  |  | — |
| Preference share redemption costs |  | — |  |  | — |  |  | — |  |  | 2.4 |
| Amortization and non-recurring expenses |  | 9.5 |  |  | 1.8 |  |  | 19.3 |  |  | 3.8 |
Operating income after tax available to ordinary shareholders |  | 48.6 |  |  | 28.6 |  |  | 103.8 |  |  | 77.8 |
Tax expense on operating income |  | 6.8 |  |  | 0.9 |  |  | 9.2 |  |  | 2.2 |
Operating income before tax available to ordinary shareholders |  | $ | 55.4 |  |  | $ | 29.5 |  |  | $ | 113.0 |  |  | $ | 80.0 |
Basic earnings per ordinary share |  |  |  |  |  |  |  |
Net (loss)/income adjusted for preference share dividends and non-controlling interest |  | $ | (0.38 | ) |  | 1.09 |  |  | $ | 0.01 |  |  | $ | 2.48 |
Add (deduct) after tax income: |  |  |  |  |  |  |  |
| Net foreign exchange losses |  | 0.55 |  |  | 0.05 |  |  | 0.29 |  |  | 0.13 |
| Net realized losses/(gains) on investments |  | 0.34 |  |  | (0.69 | ) |  | 0.97 |  |  | (1.42 | )
| Net realized loss on debt extinguishment |  | 0.14 |  |  | — |  |  | 0.14 |  |  | — |
| Preference share redemption costs |  | — |  |  | — |  |  | — |  |  | 0.04 |
| Amortization and non-recurring expenses |  | 0.16 |  |  | 0.03 |  |  | 0.32 |  |  | 0.06 |
Operating income adjusted for preference shares dividends and non-controlling interest |  | $ | 0.81 |  |  | 0.48 |  |  | $ | 1.73 |  |  | $ | 1.29 |
Diluted earnings per ordinary share |  |  |  |  |  |  |  |
Net (loss)/income adjusted for preference share dividends and non-controlling interest |  | $ | (0.38 | ) |  | 1.07 |  |  | $ | 0.01 |  |  | $ | 2.43 |
Add (deduct) after tax income: |  |  |  |  |  |  |  |
| Net foreign exchange losses |  | 0.54 |  |  | 0.05 |  |  | 0.28 |  |  | 0.13 |
| Net realized losses/(gains) on investments |  | 0.34 |  |  | (0.68 | ) |  | 0.96 |  |  | (1.39 | )
| Net realized loss on debt extinguishment |  | 0.14 |  |  | — |  |  | 0.14 |  |  | — |
| Preference share redemption costs |  | — |  |  | — |  |  | — |  |  | 0.04 |
| Amortization and non-recurring expenses |  | 0.16 |  |  | 0.03 |  |  | 0.32 |  |  | 0.06 |
Operating income adjusted for preference shares dividends and non-controlling interest |  | $ | 0.80 |  |  | 0.47 |  |  | $ | 1.71 |  |  | $ | 1.27 |

The basic and diluted number of ordinary shares for the three months ended June 30, 2018 is the same, as the inclusion of dilutive securities in a loss-making period would be anti-dilutive.
22

| ASPEN INSURANCE HOLDINGS LIMITED
Worldwide Natural Catastrophe Exposures: Major Peril Zones as at July 1, 2018
|  | 100 YEAR RETURN PERIOD AS % OF TOTAL SHAREHOLDERS’ EQUITY AND IN $ MM(1) |  | 250 YEAR RETURN PERIOD AS % OF TOTAL SHAREHOLDERS’ EQUITY AND IN $ MM(1) |

--------------------------------

|  | 1 in 100 year tolerance: 17.5% of total shareholders’ equity |  | 1 in 250 year tolerance: 25.0% of total shareholders’ equity |
| The Probable Maximum Losses ("PMLs") are net of reinsurance and Aspen Capital Markets' third-party capital. |

(1) Based on shareholders' equity of $2,825.0 million (excluding non-controlling interest) as at June 30, 2018. The estimates reflect Aspen's view of the modelled maximum losses at the return periods shown which include input from various third party vendor models and Aspen's proprietary adjustments to these models and planned reinsurance purchases. Catastrophe loss experience may materially differ from the modelled PMLs due to limitations in one or more of the models or uncertainties in the application of policy terms and limits.
23