After another playoff disappointment behind them the T-Wolves started the 2008–2009 season looking to take the next step and win the Kent Cup.

The T-Wolves came out on top winning the deciding game 3-2 thanks to Andrew White, who scored all three of the Timberwolves goals.

Summerside was riding high having just swept the Dieppe Commandos, and they swept the series on their way to winning the Kent Cup, making it the second straight season that the Timberwolves were beaten in the Meek Division final (the previous year they were defeated by the Woodstock Slammers in six games.)

Early in the 2022-23 season, after a few years of futility, the Wolves parted ways with head coach and general manager Rob MacDonald, who had been with the team since the 2011-12 campaign.

The team ended up having its best regular season since 2016-17 after naming Kory Baker as his replacement, but fell to the Edmundston Blizzard in the Eastlink North Division semifinals.