Chesswood Announces Q3 Results and Dividend Increase Record New Business, Strong Net Income and a Portfolio Milestone

TORONTO, November 9, 2016 – Chesswood Group Limited (the “Company” or “Chesswood”) (TSX: CHW) announced today its results for the three and nine months ended September 30, 2016, as well as an increase in its monthly dividend.

The Company generated operating earnings of $7.2 million in the third quarter this year, compared to $6.8 million in the third quarter of last year. Net Income was $5.1 million compared to $3.1 for the same quarter in 2015.

Chesswood’s originations in its equipment finance businesses increased by 55% over the third quarter of last year, setting another quarterly record for new business. “We’re proud of achieving another milestone in the growth of our commercial portfolio as it exceeded $500 million in gross receivables for the first time.” said Barry Shafran, Chesswood’s President and CEO.

“Our net income was also excellent this quarter while our operating earnings were impacted by a $1.9 million increase in our non-cash portfolio reserve on behalf of our non-prime U.S. equipment finance portfolio. While our charge-offs in this portfolio were the same as in the last quarter, higher delinquencies drove our reserve increase, consistent with the pattern of seasonality we typically encounter as collections slow in the last four months of the year” added Shafran.

On a nine month basis Chesswood’s operating earnings were $24.3 million, an increase of 14% or $3.1 million over the same period in 2015.

“We are also very pleased to provide our shareholders with an increase in our monthly dividend, from $0.065 per share to $0.07 per share, for an increase of 7.7%” added Mr. Shafran.”Our free cash flow has grown consistently over the past three years, since we last raised our dividend in November 2013. Our annualized yield will now rise to 7.3% based on yesterday’s closing price” said Mr. Shafran. The dividend will be payable to shareholders of record at the close of business on November 30, 2016 and will be paid on December 15, 2016. Chesswood has designated its dividends as eligible dividends for purposes of the Income Tax Act (Canada).

Non-GAAP Measures

References to Adjusted EBITDA and Operating Income are not recognized measures under International Financial Reporting Standards and do not have standard meanings. Accordingly, these measures may not be comparable to similar measures presented by other issuers.

Please refer to the Company’s Management Discussion and Analysis for the three and nine months ended September 30, 2016 for additional information concerning these measures and a reconciliation of these measures to the Company’s consolidated net income for the period.

About Chesswood Group Limited

The Company operates in the financial services industry with operating businesses in both Canada and the U.S. To learn more about Chesswood, visit www.ChesswoodGroup.com.

The separate websites of Chesswood Group Limited’s operating businesses are at www.PawneeLeasing.com and www.BlueChipLeasing.com

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For more information contact: Barry Shafran Chesswood Group Limited 416-386-3099 bshafran@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.

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

Fort Collins, CO, June 13, 2016 – Pawnee Leasing Corporation announced that it completed its business relocation to 3801 Automation Way in Fort Collins, Colorado.

“After 12 years at Centre Avenue, Pawnee Leasing Corporation moved on June 10. Our stand alone facility has been a fantastic home for Pawnee, but we finally ran out of space in the building this spring as our employee team has grown along with the significant growth of our business. It wasn’t cost effective to build on to the existing building to accommodate our future growth plans, so we have new space that allows our entire team to be together in one single open space in a larger office building in southeast Fort Collins.” said Gary Souverein, Pawnee’s President.

 

Pawnee Leasing Corporation, exclusively serving the equipment leasing broker and lessor channel since 1982, has expanded its product line over the last ten years and now offers financing not only for start-ups and “B” credits but also for application-only “A” credits to $150,000 to select broker and lessor partners, at competitive rates.

Souverein added, “We’re looking forward to settling in to our new home and expect that it will be as great as our last one at Centre Avenue. More importantly, I’m looking forward to each of our employees growing, learning and succeeding as a Team in our new home as we set our eyes on new milestones and achievements for Pawnee.”

Pawnee Leasing Corporation, providing lease financing in the lower 48 states since 1982, purchases small-ticket “Start-Up”, “C”, “B” and “A” credit transactions from a national network of brokers/ lessors. Pawnee Leasing also supports contract servicing for its sister-company, Windset Capital Corporation, a working capital funding source founded in 2013.

For more information please contact info@pawneeleasing.com www.pawneeleasing.com

Pawnee Leasing Corporation is a Chesswood Group Limited company traded on the Toronto Stock Exchange – TSX:CHW – www.chesswoodgroup.com

Riverton, UT, September 16, 2016 – Windset Capital Corporation (“Windset”), a subsidiary of
Chesswood Group Limited (“Chesswood”), announced today that it will discontinue accepting new
loan applications from its brokers and independent sales organization network effective September
26, 2016.

“After three years of serving the short-term working capital market and dedicating 100% of
Windset’s resources to the broker/ISO community, we have made the strategic decision to exit the
working capital loan market and focus solely on our growing equipment finance businesses.” said
Barry Shafran, Chesswood’s President and CEO.

“We have made the decision to focus our organization on our growing and more profitable business
activities in the equipment finance market” added Gary Souverein, Windset and Pawnee Leasing
Corporation’s President. “While we have continued to manage Windset profitably, our longer term
outlook on the changing fundamentals of the working capital loan market have made us
uncomfortable with the risk-return profile. We appreciate the many relationships we have made
since 2013 and we will continue to fund all of our partners’ approved applications” said Souverein.

Windset will no longer accept new loan applications effective Monday, September 26, 2016.
Windset will complete and fund all open and valid approvals and will continue to service all of the
loans in its portfolio, for the entire duration of their terms.

About Chesswood Group Limited

Chesswood Group Limited, a public company traded on the Toronto Stock Exchange (TSX:CHW),
operates in the financial services industry with equipment finance businesses in both Canada and
the U.S. To learn more about Chesswood Group, visit www.ChesswoodGroup.com.

Founded in 1982, Pawnee Leasing Corporation is a market-leading national small-ticket equipment
finance business specializing in lending to small and medium sized businesses in all credit profiles
including start-ups, with transactions up to $150,000.

For more information visit www.Chesswood.com,
www.PawneeLeasing.com , www.WindsetCapital.com

For more information contact:
Barry Shafran
President & CEO President
Chesswood Group Limited
416-386-3099
bshafran@chesswoodgroup.com

Gary Souverein
President
Windset Capital Corporation and
Pawnee Leasing Corporation
800-864-4266
gary@windsetcapital.com gary@pawneeleasing.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.