How close are Canada's NHL teams to breaking our Stanley Cup drought?

Hamilton Spectator

19-06-2025

The 'Dominion Hockey Challenge Cup' donated by Lord Stanley of Preston was supposed to be awarded to the best Canadian hockey team when it was commissioned in 1892.
As the Stanley Cup moved from an amateur challenge Cup to a professional annual trophy, 40 of the first 41 champions were Canadian, interrupted only by those pesky Seattle Metropolitans in 1917.
Needless to say, Canadian hockey teams haven't had a run like that in a good long while. As the
Edmonton Oilers flamed out for the second year
in a row, losing again to the Florida Panthers, we're reminded — because we can't help ourselves — that a Canadian team hasn't won the Stanley Cup in 32 years.
You can blame the salary cap, or that Canadian taxes make it harder to attract talent. You can say the pressure too intense in Canadian markets. Blame the border if you want.
Regardless, Canadian teams have come close since Montreal last won the Cup in 1993. Calgary in 2004, Edmonton again in 2006, Vancouver in 2011, and Montreal in 2021.
Are Canadian teams in the NHL now just lovable losers, like Charlie Brown having the football pulled from him by Lucy every time?
Or are Canadians eternal optimists when it comes to hockey?
Here's a look at the seven Canadian teams, and their chances of bringing the Stanley Cup home anytime soon. They are presented in order from their last Stanley Cup.
Stanley Cup titles:
24, last in 1993.
A handful of players remain from their unexpected run to the Cup final in 2021 and a rebuilding process since then paid off with a surprising playoff appearance this season. GM Kent Hughes has so far had a patient approach the fan-base bought into, and has an array of young talent led by rookie of the year Lane Hutson. A return to their status of Les Glorieux seems only a season or two away.
Stanley Cup prognosis:
In the next five years.
Stanley Cup titles:
Five, last in 1991.
When you have two of the best players on the planet, you always have a chance. Leon Draisaitl's league-leading $14 million (U.S.) a year deal kicks in July 1. But they only have Connor McDavid guaranteed for one more year. They've been to the final two years in a row. Having the second-best goaltender in a series is not a good idea. GM Stan Bowman has to be on the lookout for a goalie. He doesn't have a great deal of cap wiggle room, about $12 million, and his priority will have to be restricted free agent defenceman Evan Bouchard.
Cup prognosis:
2026 or bust.
Stanley Cup titles:
One in 1989
The Flames seem caught in the murky middle. Good enough to almost make the playoffs, not bad enough to get franchise cornerstone draft picks. GM Craig Conroy has a building block in goalie Dustin Wolf. But there's not a lot of support for Nazem Kadri and Jonathan Huberdeau. Conroy has more than $27 million in cap space this summer, but this team will be closer to a Stanley Cup contender by tanking the next couple of years.
Cup prognosis:
Get back to us in the 2030s.
Stanley Cup titles:
13, last in 1967
With or without Mitch Marner, the Maple Leafs have an impressive array of talent, perhaps the highest level of talent in their post-Stanley Cup existence. That's a long time — 58 years, not that anybody's counting. Put them down for at least 100 points next season, maybe even the President's Trophy.
The playoffs, though? That's quite another story. We've all seen it. Their lack of success is its own tragicomedy. This core group should have played for a Cup by now. What's the definition of insanity?
Cup prognosis:
There's always next year.
Stanley Cup titles:
Four, last in 1927 (a very different franchise with the same name)
It took this core of young players longer than expected to make the playoffs. But the only thing more true than the Leafs bowing out early is the Leafs beating Ottawa in the post-season. The Brady Tkachuk-led team seems ready to make the leap. Jake Sanderson is the real deal on defence. Linus Ullmark is a quality goalie. Travis Green is a quality coach. And the ownership group led by Michael Andlauer seems ready to spend to contend.
Cup prognosis:
Coming soon to the nation's capital.
Stanley Cup titles:
0, last appeared in final in 2011
They are a melodrama all unto themselves, and comic relief to the fan bases of the other Canadian teams. How they ruined what they had as recently as two years ago seems improbable. Once, the question was how far could elite defenceman Quinn Hughes and top forward Elias Pettersson take them? Now the questions are what happened to Pettersson, and will Hughes stay or try — as president Jim Rutherford mused publicly — to join his brothers Jack and Luke in New Jersey?
Cup prognosis:
Perhaps more cursed than the Maple Leafs.
Stanley Cup titles:
0, never appeared in final.
Can you imagine having a team this good and failing to make it to the Cup final? I guess you can if you follow the Leafs closely. That's life in Winnipeg, too. Great regular seasons. Early playoff exits. The thing that's hard to wrap your head around is Connor Hellebuyck. He won the Vezina this season as the league's top goalie. He always has good regular seasons, but he's a shadow of himself in the playoffs.
A team that believes it has trouble attracting talent managed to get its top stars — Hellebuyck included — to commit. Now it's easy to wonder if the Jets committed to the wrong group.
Cup prognosis:
Perennial also-rans.