It has been decades since a Canadian team last hoisted the Stanley Cup, a drought that weighs heavily on the hearts of hockey fans across the nation.
However, as the 2025 playoffs unfold, a renewed sense of optimism is palpable. The Toronto Maple Leafs, Edmonton Oilers, and Winnipeg Jets all successfully navigated the first round, positioning themselves just one step away from the conference finals.
The journey ahead is undoubtedly challenging, but with three contenders still in the mix, the dream of ending the decades-long drought remains alive.
Canada’s Stanley Cup Drought Hits 32 Years
It’s been 32 years since a Canadian team last lifted the Stanley Cup. The Montreal Canadiens were the last to do it, defeating the Los Angeles Kings in five games in the 1993 Stanley Cup Finals.
That June 9 win is still a treasured memory for Canadian fans. While Jurassic Park dominated theaters and Janet Jackson topped the music charts, Montreal was celebrating what has since become Canada’s last Stanley Cup victory.
Since then, Canadian teams have had chances — seven made it to the Final — but none have finished the job. Most recently, the Oilers reached the 2024 Final but fell short. The Cup has remained in the United States ever since.
This year brings new hope. Toronto, Edmonton, and Winnipeg are all through to Round 2.
The Maple Leafs ousted the rival Ottawa Senators in six games and now face the defending champion Florida Panthers. Edmonton dropped the first two games to the Kings but stormed back with four straight wins and will now face the Vegas Golden Knights. Winnipeg outlasted the St. Louis Blues in a grueling seven-game series and now preps for the Dallas Stars.
It’s the first time since 2017 that five Canadian teams made the playoffs. Three are still standing—and fans can’t help but wonder: Could this be the year the Cup finally comes back north?
Canada’s Remaining Hopefuls: Leafs, Jets, and Oilers Chase History
The Maple Leafs are chasing a title that’s eluded them since 1967. With stars like Auston Matthews, William Nylander, and Mitch Marner, Toronto’s offense is potent, but their postseason track record continues to be a point of concern. They’ll have to get past a battle-tested Panthers squad to keep moving.
Winnipeg enters the second round after claiming the Presidents’ Trophy, a distinction that brings both pride and pressure. Only two of the last 17 teams to earn that title went on to win it all. The Jets are without forward Nikolaj Ehlers, and goalie Connor Hellebuyck has shown some playoff inconsistency, both of which could affect their chances against Dallas.
Then there’s Edmonton, still riding momentum from a run to last year’s Final. With Connor McDavid and Leon Draisaitl leading the way, the Oilers are a threat to anyone. But they’ll have to do it without defenseman Mattias Ekholm, whose absence could complicate things on the blue line.
There’s no denying the odds are steep. But with three contenders still alive, Canadian fans are daring to dream. Could 2025 finally be the year hockey’s most prized trophy returns home?