Chesswood Announces Record First Quarter in 2016

Results Reflect 34% Increase in Operating Income
and Gain on the Sale of EcoHome Financial

TORONTO, May 12, 2016 – Chesswood Group Limited (the “Company” or “Chesswood”)
(TSX: CHW) announced today its results for the first quarter of 2016, ended March 31, 2016.

Net income was $12.2 million, an increase of $8.7 million from the $3.5 million in net income
in the first quarter of 2015. Operating income was $8.1 million compared to $6.0 million, in
the same quarter of last year, a 34% improvement. Chesswood’s first quarter was most
notable for strong originations, growing operating earnings and a gain on the sale of
EcoHome Financial, which was completed in February. While a significant portion of the
increase in net income was attributable to the gain on sale of EcoHome Financial, the
healthy increases in operating income and Adjusted EBITDA were entirely the result of
growth in our operating businesses.

“Our operations continue to generate increasing profitability as our portfolios expand” said
Barry Shafran, Chesswood’s President and CEO. “This quarter’s results also reflect our gain
on the sale of our former EcoHome Financial consumer business, a gain we shared with our
shareholders through a special dividend paid in March” Shafran added.

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 months
and year ended March 31, 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 primarily 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,
www.WindsetCapital.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.