Last time a Canadian team won the Stanley Cup? Canadiens, Oilers and Senators vying to end 32-year drought

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Hockey fans in Canada have exhibited quite a bit of patience waiting for the Stanley Cup to make its return north of the border. It's been 33 years since a Canadian team hoisted hockey's ultimate prize, but that drought could come to an end in the 2026 Stanley Cup Playoffs.

On June 9, 1993, the Montreal Canadiens passed around the Stanley Cup after beating the Los Angeles Kings in five games. Jurassic Park was mauling its competition at the box office. Roseanne and Home Improvement were on just about every TV in America. Janet Jackson's "That's the Way Love Goes" was topping the billboard charts.

Since then, the Stanley Cup has taken up residence in the United States for 32 straight seasons following the Panthers' latest championship in 2025. The good news for our friends north of the border is that there a few strong Cup contenders in the playoff field this year.

Let's start with the Canadiens, the last Canadian team to raise a banner. They are a young and electric bunch led by Nick Suzuki and Cole Caufield. Those two have formed one of hockey's most lethal duos, and they have help from other rising stars on the roster. Former No. 1 pick Juraj Slafkovsky is finally living up to that draft pedigree, and Lane Hutson looks like a future Norris Trophy winner on the blue line. That said, there are depth concerns with this group, and a first-round matchup against the Tampa Bay Lightning is awfully daunting.

The Edmonton Oilers are back and looking to finish the job after falling just short of a Cup in each of the last two seasons. Fortunately for the Oilers, the Panthers did not make the playoffs this season. Unfortunately for the Oilers, Leon Draisaitl's injury status is still unknown. He's resumed skating with the team, but he's not quite ready for game action. That puts even more pressure on the shoulders of Connor McDavid, but if there is anyone who can drag a team to a Cup, it's him.

Finally, following a late-season surge, the Ottawa Senators are in the playoffs for the second straight year. They endured a first-round exit last season -- and while their first-round matchup against the Carolina Hurricanes will be tough -- they have the goods to pull off an upset. Ottawa is an incredibly stingy team on defense, and it has enough offense to do some damage with Tim Stutzle and Brady Tkachuk leading the charge. The question is whether the goaltending will hold up after an uneven regular season.