Stanley Cup Playoffs: Canada’s Best Shot in Decades to Bring the Cup Home

Image Credit, Tom Glod

After years of heartbreak, rebuilding, and falling just short, this might finally be the year the Stanley Cup returns home to Canada. With five Canadian teams punching their tickets to the 2025 NHL Playoffs, the odds haven’t looked this promising since the early 2000s. And if the regular season was any indication, this postseason could be the best chance in decades for a Canadian franchise to reclaim hockey’s ultimate prize.

Leading the charge are the Edmonton Oilers—fast, fierce, and firing on all cylinders. The defending Western Conference champions aren’t just coasting into the postseason; they’re cruising. With Connor McDavid and Leon Draisaitl continuing to operate like hockey cyborgs, the Oilers have managed to combine blistering offense with a much-improved blue line. They’ve been here before, and this time, they look even more prepared to finish what they started.

Meanwhile, the Winnipeg Jets have stunned just about everyone by locking up their division. With one of the league’s best goaltenders in Connor Hellebuyck and a no-nonsense defense, the Jets play a bruising, disciplined style of hockey that’s built for the grind of the postseason. Their top-six forwards have shown they can score, but it’s their depth and grit that make them a legitimate threat to upset anyone in their path.

And they’re not alone. Toronto, Vancouver, and Montreal are all in the dance, adding to the buzz and belief north of the 49th parallel. Toronto, always a media magnet, enters with a balanced roster and the lingering sting of repeated early exits. Vancouver’s young core has matured rapidly, giving Canucks fans their most hopeful spring in years. Montreal, though a wildcard, carries the weight of a rich history and a young, hungry roster looking to make noise.

It’s not just about talent—it’s about timing. For the first time in years, Canada has multiple teams that not only made the playoffs but did so with momentum. The Oilers have the star power, the Jets have the structure, and Toronto, Vancouver, and Montreal all bring unique strengths to the table. Statistically, the numbers alone give Canada a stronger-than-usual probability of ending its decades-long drought since the Canadiens last hoisted the Cup in 1993.

But this is more than a numbers game. It’s about pride. For a country that breathes hockey, the absence of the Stanley Cup from Canadian soil has been a source of national frustration. Each spring, Canadians rally behind their teams, and when those fall, they rally behind any Canadian team left standing. It’s about reclaiming a symbol that feels inherently Canadian but has eluded the nation for 32 long years.

This postseason could be different. The Oilers are built to win now. The Jets are surging at the right time. And with five Canadian teams in the mix, the math—and the heart—finally feel like they’re in alignment.

It won’t be easy. The road to the Cup is brutal. But for the first time in a long time, the belief is real. Canada isn’t just hoping this year. It’s expecting. And if everything clicks, 2025 may be remembered as the year the Stanley Cup finally came back home.