UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 13D

(Rule 13d-101)

UNDER THE SECURITIES EXCHANGE ACT OF 1934

(Amendment No. 2)

Kingsway Financial Services Inc.

(Name of Issuer)

Common Stock, no par value per share

(Title of Class of Securities)

496904202

(CUSIP Number)

Terence M. Kavanagh

45 St. Clair Avenue West, Suite 400

Toronto, Ontario, Canada M4V 1K9

Telephone: (416) 923-1477

(Name, Address and Telephone Number of Person Authorized to Receive Notices and Communications)

September 6, 2013

(Date of Event which Requires Filing of this Statement)

If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of Rule 13d-1(e), 13d-1(f) or 13d-1(g), check the following box  ¨.

This Amendment No. 2 to Schedule 13D (this “Amendment”) amends the Statement on Schedule 13D filed on March 5, 2009, as previously amended on December 12, 2012 (the “Schedule 13D”) by Oakmont Capital Inc., an Ontario corporation (“Oakmont”), E.J.K. Holdings Inc., an Ontario corporation (“EJK”), 1272562 Ontario Inc., an Ontario corporation (“1272562”), and Gregory P. Hannon and Terence M. Kavanagh, each of whom are citizens of Canada (collectively, the “Reporting Persons”). Capitalized terms used herein not otherwise defined shall have the meaning ascribed to them in the Schedule 13D. All references to shares of common stock in this Amendment have been adjusted for the rights offering which expired on September 6, 2013 (the “Rights Offering”).

ITEM 3. SOURCE AND AMOUNT OF FUNDS OR OTHER CONSIDERATIONS.

Item 3 of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following:

The aggregate purchase price of the 1,538,750 Shares purchased by the Reporting Persons was Cdn $28,980,614 (including commissions). The source of funding for the purchase of these Shares was general working capital of each of Oakmont, EJK and 1272562 and personal funds of each of Mssrs. Kavanagh and Hannon.

Item 4. PURPOSE OF TRANSACTION.

Item 4 of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following:

A description of transactions taken with respect to the Shares is included below in Item 5(c). The Reporting Persons have acquired the Shares of the Issuer for investment purposes.

The Reporting Persons intend to monitor the business and affairs of the Issuer, including its financial performance, and depending upon these factors, market conditions and other factors, the Reporting Persons may acquire additional Shares as they deem appropriate, in open market purchases, privately negotiated transactions or otherwise. Alternatively, the Reporting Persons may dispose of some or all of their Shares in the open market, in privately negotiated transactions or otherwise. Except as described herein, no Reporting Person has any plans or proposals which relate to, or could result in, any of the matters referred to in paragraphs (a) through (j), inclusive, of Item 4 of Schedule 13D.

Item 5. INTEREST IN SECURITIES OF THE ISSUER.

Item 5 of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following:

(a) As of the close of business on September 6, 2013, the Reporting Persons may be deemed to beneficially own, in the aggregate, 1,538,750 Shares, representing approximately 9.38% of the Issuer’s outstanding Shares (based upon the 16,396,727 Shares stated to be outstanding following the closing of the Rights offering).

(b) Oakmont has sole voting power and sole dispositive power with respect to the 1,456,250 Shares that it owns directly. Oakmont may be deemed to be a beneficial owner of the balance of the 1,538,750 Shares beneficially owned by the Group, by virtue of its participation in the Group. EJK has sole voting power and sole dispositive power with respect to the 6,000 Shares that it owns directly. EJK has shared voting power and shared dispositive power with respect to the 1,456,250 Shares owned directly by Oakmont, by virtue of EJK’s ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. EJK may be deemed to be a beneficial owner of the balance of the 1,538,750 Shares beneficially owned by the Group, by virtue of its participation in the Group.

1272562 has sole voting and sole dispositive power with respect to 3,000 Shares that it owns directly. 1272562 has shared voting power and shared dispositive power with respect to the 1,456,250 Shares owned directly by Oakmont, by virtue of its ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. 1272562 may be deemed to be a beneficial owner of the balance of the 1,538,750 Shares beneficially owned by the Group, by virtue of its participation in the Group.

Mr. Kavanagh has sole voting power and sole dispositive power with respect to 26,875 Shares owned through a self-directed Retirement Savings Plan, 1,750 Shares owned directly and 125 Shares owned directly by a trust for his nephew (Mr. Kavanagh is the sole trustee). Mr. Kavanagh has shared voting power and shared dispositive power with respect to the following Shares:

(i) the 6,000 Shares owned directly by EJK, by virtue of Mr. Kavanagh’s ownership of all of the outstanding voting stock of EJK; and (ii) the 1,456,250 Shares owned directly by Oakmont, by virtue of Mr. Kavanagh’s ownership of all the outstanding voting stock of EJK, and EJK’s ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont.

Mr. Kavanagh may be deemed to be a beneficial owner of the balance of the 1,538,750 Shares beneficially owned by the Group, by virtue of his participation in the Group.

Mr. Kavanagh’s sister owns directly and through a registered retirement savings account 10,500 Shares and his mother owns, directly and through a Retirement Income Fund, 15,000 Shares, as to which Mr. Kavanagh disclaims beneficial ownership.

Mr. Hannon has sole voting power and sole dispositive power with respect to the following Shares:

(i) the 22,500 Shares owned directly by him or through a self-directed Retirement Savings Plan; and (ii) the 4,500 Shares owned directly by two trusts for Mr. Hannon’s children; Mr. Hannon is the sole trustee of each such trust.

Mr. Hannon has shared voting power and shared dispositive power with respect to the following Shares:

(i) the 3,000 Shares owned directly by 1272562, by virtue of Mr. Hannon’s ownership of all of the outstanding voting stock of 1272562;

(ii) the 4,000 Shares owned directly by Gilter Inc., an Ontario corporation of which all of the outstanding voting stock is owned by the Gregory Hannon Family Trust, of which Mr. Hannon is one of two trustees;

(iii) the 1,456,250 Shares owned directly by Oakmont, by virtue of his ownership all of the capital stock of 1272562, and 1272562’s ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont; and

(iv) the 13,750 Shares owned directly by Mr. Hannon’s spouse.

Mr. Hannon may be deemed to be a beneficial owner of the balance of the 1,538,750 Shares beneficially owned by the Group, by virtue of his participation in the Group.

(c) In connection with the Rights Offering, Oakmont Capital Inc. purchased 381,250 Units for US $4.00 per Unit, entitling Oakmont Capital Inc. to 381,250 Shares, 381,250 Series A Warrants and 381,250 Series B Warrants. Each Series A Warrant and Series B Warrant entitles the holder thereof, subject to the terms and conditions of such warrants, to purchase one Share. Additional information regarding the terms of the warrants and the Rights Offering can be found in the related prospectus of the Company dated August 9, 2013. In addition, the following purchases were made by Oakmont Capital Inc. since the filing of the previous amendment to the Schedule 13D.

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

SCHEDULE A

DIRECTORS AND EXECUTIVE OFFICERS OF THE REPORTING PERSONS

The following sets forth the name, position and principal occupation of each director and executive officer of Oakmont, EJK and 1272562. Each such person is a citizen of Canada. The business address of each such person is 45 St. Clair Avenue West, Suite 400, Toronto, Ontario, Canada M4V 1K9. To the best of the Reporting Persons’ knowledge, except as set forth in this Statement on Schedule 13D, none of the directors or executive officers of the Reporting Person owns any Shares of the Issuer.