<DOCUMENT>
<TYPE>EX-10.39
<SEQUENCE>53
<FILENAME>ex10-39_14663.txt
<DESCRIPTION>300,000 SHARE ZUCKER STOCK OPTION GRANT
<TEXT>
                                                                   EXHIBIT 10.39
                                                                   -------------

                            BRIDGELINE SOFTWARE, INC.

                               STOCK OPTION GRANT

OPTIONEE: Brett Zucker

         Bridgeline Software, Inc. (hereinafter called the "Company"), pursuant
to its Stock Option Plan adopted August 30, 2000 (hereinafter called the
"Plan"), hereby grants to you, the optionee above named (hereinafter called the
"Optionee"), an option to purchase shares of the $.001 par value common stock of
the Company (hereinafter called the "Common Stock"). The options granted will be
Incentive Options as defined in the Plan.

         The details of your option are as follows:

1. The total number of shares of Common Stock subject to this option is 300,000.
This option shall become exercisable as follows:

         Installment     Number of Shares     First Date Exercise is Permitted
         -----------     ----------------     --------------------------------

              1               100,000                    June 1, 2006
              2               100,000                    June 1, 2007
              3               100,000                    June 1, 2008

              TOTAL           300,000

2. The term of this option commences on the date hereof and terminates 10 years
hereafter on June 1, 2015. This option is not transferable, except at death by
will or the laws of descent and distribution, and is exercisable during your
life only by you. No assignment or transfer of the option, or of the rights
represented thereby, whether voluntary or involuntary, by operation of law or
otherwise, except by will or the laws of descent and distribution, shall vest in
the assignee or transferee any interest or right herein whatsoever, but
immediately upon any attempt to assign or transfer an option the same shall
terminate and be of no force or effect.

3. The exercise price of this option is one dollar ($1.00) per share.

4. a. You may exercise this option to purchase all or any part of your allotment
which has accrued to you, at any time during the term of this option, but not
thereafter, by depositing with the Secretary or Assistant Secretary of the
Company notice in writing, designating the number of shares as to which you are
exercising your option, accompanied by payment in full for such number of
shares; provided, however, that not less than 100 shares may be purchased upon
any one exercise of the option granted hereby unless the number of shares
purchased at such time is the total number of shares in respect of which the
option hereby granted is then exercisable.

<PAGE>

         b. Payment shall be in the form of cash, certified check, bank draft or
postal or express money order payable to the order of the Company in United
States Dollars. If the Board of Directors of the Company or an authorized
committee of the Board has, pursuant to subparagraph 6.2 of the Plan, authorized
payment in stock of the Company, payment, in whole or in part, may be in the
form of a certificate or certificates representing stock of the Company at its
then value.

         c. Following receipt of such notice and required payment and compliance
by the Optionee or other person entitled to exercise the option with any
limitations and conditions imposed by this grant, the Company shall thereafter
cause its transfer agent and registrar to issue and deliver to the Optionee (or
other person entitled to exercise the option) as soon as practically possible a
certificate or certificates for such number of shares registered in the name of
the Optionee or such other person entitled to exercise the option, as the case
may be.

         d. In addition, this option shall be considered to be fully accrued and
shall be exercisable in said manner during the 10 day period following the
occurrence of any of the events described in subparagraph 10.3 of the Plan.

5. This option is subject to (a) all the provisions of the Plan, a copy of which
is attached hereto and is specifically incorporated by reference herein, and (b)
to all interpretations, rules and regulations which may from time to time be
promulgated and adopted pursuant to such Plan.

6. The Company is under no obligation to register the shares of Common Stock
purchased upon exercise of this option under the Securities Act of 1933.

7. Any dispute or disagreement which shall arise under, or as a result of, or
pursuant to, this Agreement shall be determined by the Board of Directors of the
Company in its absolute and uncontrolled discretion, and any such determination
or any other determination by the Board of Directors under or pursuant to this
Agreement and any interpretation by the Board of Directors of the terms of this
Agreement, shall be final, binding and conclusive on all persons affected
thereby.

8. Any notice which either party hereto may be required or permitted to give to
the other shall be in writing and may be delivered personally or by mail,
postage prepaid, addressed as follows: to the President of the Company, at
Bridgeline Software, Inc. at 130 New Boston Street, Woburn, Massachusetts 01801,
or at such other address as the Company by notice to the Optionee may designate
in writing from time to time; to the Optionee, at his address as the Optionee,
by notice to the President of the Company, may designate in writing from time to
time.

9. The Company shall endorse an appropriate legend on certificates of Common
Stock issued to the Optionee pursuant to the Plan to evidence the
representations of the Optionee under paragraph 8 of the Plan.

                                        2
<PAGE>

         Dated as of the 1st day of June, 2005.

                                         BRIDGELINE SOFTWARE, INC.


                                         By: /S/ THOMAS MASSIE
                                             ----------------------------
                                             President

                                             Duly authorized on behalf of the
                                             Board of Directors

         The undersigned accepts the foregoing option and agrees to all the
terms and conditions thereof, acknowledging hereby receipt of a copy of the
Stock Option Plan.

         Dated as of the 1st day of June, 2005.


                                             /S/ BRETT ZUCKER
                                             -----------------------------
                                             Brett Zucker, Optionee






















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</DOCUMENT>
