SEVERANCE AGREEMENT AND GENERAL RELEASE

Exhibit 10.1

SEVERANCE AGREEMENT AND GENERAL RELEASE

(PLEASE READ CAREFULLY. THIS AGREEMENT AND GENERAL RELEASE HAS IMPORTANT LEGAL CONSEQUENCES.)

     This Severance Agreement and General Release (the “Agreement”) is between DealerTrack Holdings, Inc. (the “Company” or “we”) and Robert Cox (“Employee” or “you”). The term “Company” includes parents, subsidiaries or related companies, as well as their directors, officers, shareholders, employees, agents, attorneys, and successors.

     WHEREAS, the Company and the Employee have entered into an Amended and Restated Senior Executive Employment Agreement dated as of August 8, 2007 and amended by Amendment No. 1 to Amended and Restated Executive Employment Agreement, dated December 31, 2008 (the “Employment Agreement”); and

     WHEREAS, the Company has elected to terminate Employee’s employment without cause pursuant to the Employment Agreement; and

     WHEREAS, for the consideration specified below, the Employee is willing to execute this Agreement.

     NOW, THEREFORE, IT IS HEREBY AGREED THAT:

     1. Employee’s last date of employment with the Company shall be March 2, 2009 (the “Termination Date”).

     2. Employee’s employment by the Company shall terminate on the Termination Date. Employee hereby resigns as an officer, director, employee, member, manager and in any other capacity with the Company and each of its affiliates effective as of the Termination Date and confirms that as of the Termination Date he shall not hold any such position with the Company or any of its affiliates. The Company hereby confirms that it and each of its affiliates accepts such resignation effective as of the Termination Date. Employee agrees that following the Termination Date he shall have no consulting relationship with the Company or any of its affiliates. Employee waives any right or claim to reinstatement as an employee of the Company and any affiliate of the Company (if any) by which he was previously employed. On or promptly following (and in all events within 30 days after the Termination Date), the Company agrees to provide Employee with all amounts owed for his regular and usual salary (including, but not limited to, any severance (other than the Severance Benefits expressly provided for in, and subject to the terms of, this Agreement), overtime, bonus, accrued vacation, commissions, or other wages), reimbursement of expenses, and usual benefits, and that all payments due to Employee from the Company and its affiliates after the date of this Agreement shall be determined under this Agreement. Except as otherwise provided in this Agreement, all benefits and perquisites of employment will cease as of the Termination Date.

     3. Subject to the effective execution of the Reaffirmation of Agreement, the Company will pay Employee the following (the “Severance Benefits”):

     4. The Company and the Employee agree that as of the Termination Date, following Employee’s effective execution of the Reaffirmation of Agreement, Employee’s options to purchase the Company’s common stock will be vested and exercisable to the extent set forth on Schedule A attached hereto (the “Vested Stock Options”). The Vested Stock Options shall remain exercisable in accordance with their terms until the close of business on March 1, 2011. Additionally, all restrictions shall lapse on the number of shares of restricted common stock set forth on Schedule A attached hereto. Any and all other outstanding equity-based awards, shall be, and hereby are, terminated as of the Termination Date and Employee shall have no further rights with respect thereto or in respect thereof.

     5. Employee agrees that the execution of this Agreement is required by Section 5(d) of the Employment Agreement and that Employee would not otherwise be entitled to the Severance Payments except by executing this Agreement and the Reaffirmation of Agreement. Employee agrees and acknowledges that he is entitled to no other payments or benefits beyond the Termination Date.

     6. Employee acknowledges and agrees that the provisions of Sections 7, 8, 9 and 10 of the Employment Agreement shall survive termination of Employee’s Agreement and are hereby incorporated herein. By way of clarification, paragraph 9(a)(6) of Employee’s Agreement is limited to business operated by the Company at the date of this Agreement.

     7. The parties agree that, other than the sections of the Employment Agreement specifically referred to in this Agreement, they shall have no further obligations under the Employment Agreement.

     8.  Release . Employee, on behalf of himself, his descendants, dependents, heirs, executors, administrators, assigns, and successors, and each of them, hereby covenants not to sue and fully releases and discharges the Company and each of its parents, subsidiaries and affiliates, past and present, as well as its and their trustees, directors, officers, members, managers, partners, agents, attorneys, insurers, employees, stockholders, representatives, assigns, and successors, past and present, and each of them, hereinafter together and collectively referred to as the “Releasees,” with respect to and from any and all claims, wages, demands, rights, liens, agreements or contracts (written or oral), covenants, actions, suits, causes of action, obligations, debts, costs, expenses, attorneys’ fees, damages, judgments, orders and liabilities of whatever kind or nature in law, equity or otherwise, whether now known or unknown, suspected or unsuspected, and whether or not concealed or hidden (each, a “Claim”), which he now owns or holds or he has at any time heretofore owned or held or may in the future hold as against any of said Releasees (including, without limitation, any Claim arising out of or in any way connected with Employee’s service as an officer, director, employee, member or manager of any Releasee, Employee’s separation from his position as an officer, director, employee, manager and/or member, as applicable, of any Releasee, or any other transactions, occurrences, acts or omissions or any loss, damage or injury whatever), whether known or unknown, suspected or unsuspected, resulting from any act or omission by or on the part of said Releasees, or any of them, committed or omitted prior to the date of this Agreement including, without limiting the generality of the foregoing, any Claim under Title VII of the Civil Rights Act of 1964, the Age Discrimination in Employment Act of 1967, the Americans with Disabilities Act, the Family and Medical Leave Act of 1993, or any other federal, state or local law, regulation, or ordinance, or any Claim for severance pay, bonus, sick leave, holiday pay, vacation pay, life insurance, health or medical insurance or any other fringe benefit, workers’ compensation or disability (the “Release”); provided, however, that the foregoing release does not apply to any obligation of the Company to Employee pursuant to any of the following: (1) any equity-based awards previously granted by the Company to Employee, to the extent that such awards continue after the t