An anonymous director reports

CHESSWOOD GROUP LIMITED ANNOUNCES CLOSING OF FIRST SALE OF RECEIVABLES TO PREVIOUSLY ANNOUNCED JOINT VENTURE

Chesswood Group Ltd. has closed the first sale of receivables to the joint venture previously announced between Chesswood subsidiary Pawnee Leasing Corp. and a fund managed by Wafra Inc.

In connection with the formation of the joint venture and the closing of the first sale of receivables, Chesswood has issued to an affiliate of the Wafra fund share purchase warrants to purchase 2,083,949 Chesswood common shares exercisable until the eighth anniversary of issuance, provided that such affiliate is not permitted to exercise warrants to acquire beneficial ownership of, or control or direction over, more than 9.9 per cent of the number of then outstanding Chesswood common shares. The warrants are exercisable at $10 per common share, can be exercised at the option of the holder on a cashless basis, and has certain features to protect the holder from dilution and other material corporate events.

A total of 1,041,975 warrants vested immediately upon issuance, and the remaining warrants will vest on a linearly interpolated basis as receivables are purchased by the joint venture. The warrants and the common shares issuable upon exercise of the warrants are subject to a four-month hold period from the date of issuance in accordance with applicable Canadian securities laws.

About Chesswood Group Ltd.

Chesswood, based in Toronto, Canada, is a holding company whose subsidiaries engage in the business of specialty finance (including equipment finance throughout North America and vehicle finance and legal sector finance in Canada), as well as the origination and management of private credit alternatives for North American investors. Its shares trade on the Toronto Stock Exchange under the symbol CHW.