Mr. Ryan Marr reports

CHESSWOOD GROUP LIMITED ANNOUNCES AUGUST 2023 DIVIDEND

Chesswood Group Ltd. has declared a dividend in an amount of five cents per share for the month of August, payable on Sept. 15, 2023, to shareholders of record at the close of business on Aug. 31, 2023.

Chesswood advises that the dividend declared for the month ending Aug. 31, 2023, will be eligible dividends for the purposes of the Income Tax Act (Canada) and any similar provincial legislation.

The actions by central banks to significantly raise interest rates since Q1 2022 has affected the general business climate and levels of economic activity. Similar to many other specialty finance companies, Chesswood's increased cost of funding has temporally compressed Chesswood's net interest margins, as discussed in the company's financial reporting. On the other hand, these challenges to the company's industry may also provide competitive opportunities to stronger, more tenured players such as Chesswood's companies.

Management and the company's directors continue to evaluate portfolio performance and various interest rate scenarios on its profitability. These evaluations may result in a determination in the near term that a temporary adjustment to the company's dividend rate is appropriate to address this period of macroeconomic uncertainty and to conserve capital as the company focuses on both growth opportunities and long-term shareholder value.

About Chesswood Group Ltd.

Chesswood Group is a Toronto, Canada-based, 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. The company's shares trade on the Toronto Stock Exchange (under the symbol CHW).