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Chesswood Renews Normal Course Issuer Bid

TORONTO, ONTARIO -- (Marketwired) -- 08/21/14 -- Chesswood Group Limited ("Chesswood") (TSX:CHW) announced today that the Toronto Stock Exchange (the "TSX") has accepted its notice of intention to conduct a normal course issuer bid to enable it to purchase up to 746,331 of its 10,373,932 Common Shares ("Shares") outstanding, representing approximately 10 per cent of Chesswood's public float of 7,463,312 Shares as of August 12, 2014. The average daily trading volume of Chesswood for the past six months was 20,569, and a maximum of 5,142 Shares (being 25% of the average daily trading volume) may be purchased by Chesswood on any one day under its normal course issuer bid, except where purchases are made in accordance with "block purchases" exemptions under applicable TSX policies.

The normal course issuer bid will commence on August 25, 2014, and will terminate on the earlier of August 24, 2015, the date Chesswood completes its purchases pursuant to the notice of intention to make a normal course issuer bid filed with the TSX or the date of notice by Chesswood of termination of the bid.

During the period from August 25, 2013 to August 24, 2014 inclusively, Chesswood did not purchase any of its outstanding Common Shares under the previous normal course issuer bid.

Chesswood will make purchases on the open market through the facilities of the TSX in accordance with the rules and policies of the TSX. The price that Chesswood will pay for any such Shares will be the market price of such Shares on the TSX at the time of acquisition. Shares purchased under the bid will be cancelled.

About Chesswood Group Limited

Chesswood Group Limited is a financial services company with operating businesses in both Canada and the U.S.

To learn more about Chesswood Group Limited, visit www.ChesswoodGroup.com.

The separate websites of Chesswood Group Limited's operating businesses are at www.PawneeLeasing.com, www.nstarleasing.com, www.WindsetCapital.com, www.CaseFunding.com, and www.AcuraSherway.com.

This press release contains forward-looking statements that involve a number of risks and uncertainties because they relate to events and depend on circumstances that will occur in the future. Many factors could cause actual results and developments to differ materially from those expressed or implied by these forward-looking statements.

NO STOCK EXCHANGE, SECURITIES COMMISSION OR OTHER REGULATORY AUTHORITY HAS APPROVED OR DISAPPROVED THE INFORMATION CONTAINED HEREIN.

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