Mr. Barry Shafran reports

CHESSWOOD RENEWS NORMAL COURSE ISSUER BID AND AUTOMATIC SHARE PURCHASE PLAN

The Toronto Stock Exchange has accepted Chesswood Group Ltd.'s notice of intention to conduct a normal course issuer bid to enable it to purchase up to 1,031,791 of its 16,243,461 common shares outstanding, representing approximately 10 per cent of Chesswood's public float of 10,317,918 common shares as of Aug. 20, 2019. The average daily trading volume of Chesswood for the past six months was 19,317, and a maximum of 4,829 common shares (being approximately 25 per cent of the average daily trading volume during the preceding six months) 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 Aug. 26, 2019, and will terminate on the earlier of either: (i) Aug. 25, 2020, the date Chesswood completes its purchases pursuant to the notice of intention to make a normal course issuer bid filed with the TSX; or (ii) the date of notice by Chesswood of termination of the bid.

Chesswood previously sought and received approval from the TSX to purchase up to 1,043,895 of its outstanding common shares in connection with its previous normal course issuer bid, which expires on Aug. 24, 2019. As of Aug. 20, 2019, Chesswood had purchased 284,360 common shares through the TSX at a weighted average price of $10.2634 per share. Chesswood believes that the market price of the common shares at certain times may be attractive and that the purchase of common shares from time to time would be an appropriate use of its funds in light of potential benefits to remaining shareholders.

Chesswood will enter into an automatic share purchase plan agreement (ASPP) with a broker to allow for the purchase of common shares under the normal course issuer bid at times when Chesswood normally would not be active in the market due to regulatory restrictions or self-imposed trading blackout periods. Before entering into a blackout period, Chesswood may, but is not required to, instruct the designated broker to make purchases under the normal course issuer bid, in accordance with the terms of the ASPP. Such purchases will be determined by the broker in its sole discretion, based on parameters established by Chesswood prior to the blackout period, in accordance with TSX rules and the terms of the ASPP. The terms of the ASPP have been precleared by the TSX. Outside of these predetermined blackout periods, common shares will be purchased in accordance with management's discretion.

Chesswood will make purchases on the open market through the facilities of the TSX, in accordance with the rules and policies of the TSX or alternative trading systems in Canada. The price that Chesswood will pay for any such common shares will be the market price of such common shares on the TSX at the time of acquisition. Common shares purchased under the bid will be cancelled following purchase.

About Chesswood Group Ltd.

Through three wholly owned subsidiaries in the United States and Canada, Chesswood Group is North America's only publicly traded commercial equipment finance company that is focused on small-sized and medium-sized businesses. The company's Colorado-based Pawnee Leasing Corp., founded in 1982, finances a highly diversified portfolio of commercial equipment leases and loans through relationships with over 600 independent brokers in the United States. In Canada, Blue Chip Leasing Corp. has been originating and servicing commercial equipment leases and loans since 1996, and today operates through a nationwide network of more than 50 independent brokers.