CHESSWOOD CLOSES MARKETED SECURITIZATION FOR US$356 MILLION

TORONTO, October 25, 2021 – Chesswood Group Limited (“Chesswood”) (TSX: CHW) is pleased to announce that its subsidiary Pawnee Leasing Corporation (“Pawnee”) has closed its marketed U.S. securitization of receivables. Proceeds from this securitization totalled US$356 million and will be used to repay Pawnee’s warehouse facility and more than US$140 million of Chesswood’s corporate revolving credit facility.

“This transaction substantially improves Chesswood’s financial position by increasing liquidity and providing us with an approximate 100bps improvement in our cost-of-funds. The success of this asset-backed securitization is evidence of Pawnee’s high quality portfolio and further demonstrates Chesswood’s ability to manage treasury and funding resources, allowing us to continue to grow the business” said Ryan Marr, Chesswood’s President and CEO.

About Chesswood Group Limited

Through two wholly-owned subsidiaries in the United States and two subsidiaries in Canada, Chesswood Group Limited is North America’s only publicly traded commercial equipment finance company focused on small and medium-sized businesses. Colorado-based Pawnee Leasing Corporation, 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. Tandem Finance Inc. provides financing in the U.S. through the equipment vendor channel. In Canada, Blue Chip Leasing Corporation 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. Vault Credit Corporation specializes in equipment leases and commercial loans across Canada, allowing for customizable financing solutions while catering to a wide spectrum of credit tiers, equipment types and sectors by offering industry-leading service levels, experienced underwriters and account administrators.

Based in Toronto, Canada, Chesswood Group Limited’s shares trade on the TSX under the symbol CHW.

The websites of Chesswood Group Limited’s operating businesses are:
www.PawneeLeasing.com www.BlueChipLeasing.com
www.TandemFinance.com www.VaultCredit.com

Contact
Investor Relations: Phone: 416-386-3099 Email: investorrelations@chesswoodgroup.com
Media Inquiries: Ryan Marr, Chief Executive Officer, 416-386-3099, rmarr@chesswoodgroup.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 (including the ultimate duration and severity of the COVID-19 pandemic). By its nature, this information is subject to inherent risks and uncertainties that may be general or specific and which give rise to the possibility that expectations, forecasts, predictions, projections or conclusions will not prove to be accurate, that assumptions may not be correct and that objectives, strategic goals and priorities will not be achieved. Additional information about the risks and uncertainties of the Company’s businesses and material factors or assumptions on which information contained in forward-looking statements is based is provided in its publicly filed documents, including the Company’s annual information form and management’s discussion and analysis of the financial condition and performance, which are available electronically through the System for Electronic Document Analysis and Retrieval at www.sedar.com.

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