    <SEC-DOCUMENT>0001104659-20-060928-index.html : 20200513
    <SEC-HEADER>0001104659-20-060928.hdr.sgml : 20200513
    <ACCEPTANCE-DATETIME>20200513170134
    ACCESSION NUMBER:		0001104659-20-060928
    CONFORMED SUBMISSION TYPE:	DEF 14A
    PUBLIC DOCUMENT COUNT:		6
    CONFORMED PERIOD OF REPORT:	20200623
    FILED AS OF DATE:		20200513
    DATE AS OF CHANGE:		20200513
    EFFECTIVENESS DATE:		20200513

    FILER:

    	COMPANY DATA:
    		COMPANY CONFORMED NAME:			Wayside Technology Group, Inc.
    		CENTRAL INDEX KEY:			0000945983
    		STANDARD INDUSTRIAL CLASSIFICATION:	WHOLESALE-COMPUTER & PERIPHERAL EQUIPMENT & SOFTWARE [5045]
    		IRS NUMBER:				133136104
    		STATE OF INCORPORATION:			DE
    		FISCAL YEAR END:			1231

    	FILING VALUES:
    		FORM TYPE:		DEF 14A
    		SEC ACT:		1934 Act
    		SEC FILE NUMBER:	000-26408
    		FILM NUMBER:		20874017

    	BUSINESS ADDRESS:
    		STREET 1:		4 INDUSTRIAL WAY WEST
    		STREET 2:		SUITE 300
    		CITY:			EATONTOWN
    		STATE:			NJ
    		ZIP:			07724
    		BUSINESS PHONE:		732-389-0932

    	MAIL ADDRESS:
    		STREET 1:		4 INDUSTRIAL WAY WEST
    		STREET 2:		SUITE 300
    		CITY:			EATONTOWN
    		STATE:			NJ
    		ZIP:			07724

    	FORMER COMPANY:
    		FORMER CONFORMED NAME:	PROGRAMMERS PARADISE INC
    		DATE OF NAME CHANGE:	19950531
    </SEC-HEADER>
    <DOCUMENT>
    <TYPE>DEF 14A
    <SEQUENCE>1
    <FILENAME>tm201949d2_def14a.htm
    <DESCRIPTION>DEF 14A
    <TEXT>
    Document 1 - file: tm201949d2_def14a.htm

    </DOCUMENT>
    <DOCUMENT>
    <TYPE>GRAPHIC
    <SEQUENCE>2
    <FILENAME>tm201949d2_defc14aimg-001.jpg
    <DESCRIPTION>GRAPHIC
    <TEXT>
    Document 2 - file: tm201949d2_defc14aimg-001.jpg

    </DOCUMENT>
    <DOCUMENT>
    <TYPE>GRAPHIC
    <SEQUENCE>3
    <FILENAME>tm201949d2_defc14aimg-002.jpg
    <DESCRIPTION>GRAPHIC
    <TEXT>
    Document 3 - file: tm201949d2_defc14aimg-002.jpg

    </DOCUMENT>
    <DOCUMENT>
    <TYPE>GRAPHIC
    <SEQUENCE>4
    <FILENAME>tm201949d2_defc14aimg-003.jpg
    <DESCRIPTION>GRAPHIC
    <TEXT>
    Document 4 - file: tm201949d2_defc14aimg-003.jpg

    </DOCUMENT>
    <DOCUMENT>
    <TYPE>GRAPHIC
    <SEQUENCE>5
    <FILENAME>tm201949-2_def14aimg01.jpg
    <DESCRIPTION>GRAPHIC
    <TEXT>
    Document 5 - file: tm201949-2_def14aimg01.jpg

    </DOCUMENT>
    <DOCUMENT>
    <TYPE>GRAPHIC
    <SEQUENCE>6
    <FILENAME>tm201949-2_def14aimg02.jpg
    <DESCRIPTION>GRAPHIC
    <TEXT>
    Document 6 - file: tm201949-2_def14aimg02.jpg

    </DOCUMENT>
    </SEC-DOCUMENT>