On January 26, 2002, the Flyers set the WOHL record for largest margin in a shutout victory by defeating the Aylmer Aces by a score of 16–0.

[1][permanent dead link‍]On Tuesday March 16, 2010, the Leamington Flyers hired Head Coach Tony Piroski.

Previously, as coach of the Essex 73's, Piroski won seven Great Lakes Junior C Hockey League championships and three Clarence Schmalz Cups in nine seasons.

In spring 2011 the Flyers brought aboard OHL scout Mike Sadler as the club's general manager.

April 2, 2018, owner Abe Fehr announced that he had sold the team to five local businessman, Jason Melo, Dan Jancevski, Cam Crowder, David Halliwill & Craig Mahon.

The current version of the Leamington Flyers led by Cam Crowder and General Manager Justin Solcz, take great pride in competing for the Sutherland cup while developing players for higher levels of hockey.

The Leamington Flyers and the Ontario Hockey League's Flint Firebirds announced an affiliation agreement in June 2019 prior to the 2019–2020 season.

In the playoffs the Flyers swept the Sarnia Legionnaires and the LaSalle Vipers before defeating the St. Marys Lincolns 4–1 in the Western Conference finals.