Which team has best chances of breaking Canada’s 32-year Stanley Cup drought?

The matchups for the 2025 NHL playoffs are set after Wednesday night’s Montreal Canadiens 4-2 win over the Carolina Hurricanes. The Habs are the fifth Canadian team to make the NHL playoffs this season, giving Canada its best chance in recent history to bring the Stanley Cup back north.

So, let’s take a look at which team has the best chance of breaking Canada’s 32-year Stanley Cup drought.

Which team has best chance of breaking Canada’s 32-year Stanley Cup drought in 2025 NHL playoffs?

#5 Montreal Canadiens

According to Money Puck, the Montreal Canadiens have a 0.6% of winning the Stanley Cup this season. The Canadiens weren’t supposed to make the NHL playoffs this season as they are still considered a rebuilding team.

However, the rebuild has moved forward enough for them to nab the Eastern Conference’s second wild card spot.

The Habs have a strong forward group led by Cole Caufield, Nick Suzuki, and Patrik Laine. Nevertheless, their porous defense and questionable goaltending could doom them as the Habs will take on the Washington Capitals in the first round.

#4 Ottawa Senators

Money Puck gives the Ottawa Senators a 2.7% of winning the Cup. Those odds seem relatively low for a team that has played tough all season. The Senators had a strong regular season in which they surpassed expectations and finally made the NHL playoffs after a number of disappointing seasons.

Travis Green’s team looks poised to make noise and could upset the Toronto Maple Leafs in the first round. If that’s indeed the case, the Senators will not have an easy path as they’ll have to go through Florida before eventually reaching the Eastern Conference Final.

#3 Edmonton Oilers

The Edmonton Oilers have a 4.8% chance of returning to the Stanley Cup Final, according to Money Puck. The Oilers came within one win of the Cup last season. However, the Oilers are severely wounded with players like Connor McDavid, Leon Draisaitl, and Stuart Skinner all nursing nagging injuries.

The Oilers’ blue line has been decimated with as many as three key contributors on the shelf. While Trent Frederic and Evander Kane will be back for the postseason, there are no assurances the Oilers will be able to get past the LA Kings for the second season in a row.

If the Oilers do make it out of the first round, they could well run into the Vegas Golden Knights, the Pacific Division winner this year. While it won’t be easy, the Oilers have the firepower to take over, that is, if their main guns are healthy for the NHL playoffs.

#2 Toronto Maple Leafs

All signs point toward this being the Toronto Maple Leafs’ best chance to end their 50-plus-year Stanley Cup drought. The Leafs, led by captain Auston Matthews and 100-point scorer Mitch Marner, have transformed their style of play under coach Craig Berube.

The Leafs have been able to combine a tight-checking, grinding style with high-end scoring power under The Chief. Their goaltending is strong with Joseph Woll and Anthony Stolarz looking like two capable starters.

However, the Leafs will face the Senators who swept them during the regular-season series. If the Leafs can turn the page, they could be on track to make a deep run in the 2025 NHL playoffs. Money Puck gives the Leafs a 9.6% chance to take it all this season.

#1 Winnipeg Jets

The Presidents’ Trophy winners have the best chance to win the Stanley Cup. According to Puck Money, the Winnipeg Jets have a 10.6% of winning the Stanley Cup. With all-world netminder Connor Hellebuyck, the Jets have as good a chance as any team.

The Jets also boast a solid offensive attack with a reliable defensive core. However, the regular season is one thing. The postseason is a completely different beast. The Jets will face the St. Louis Blues, the hottest team in the second half of the season.

The Jets could be primed for a first-round upset unless they overwhelm the Blues from the start. Considering the Jets’ dominance this season, they could end Canada’s Stanley Cup drought since the Montreal Canadiens defeated the LA Kings in 1993.

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alt=”Nestor Quixtan” height=”72″ width=”72″>

Nestor is an NHL and MLB writer at Sportskeeda with over 10 years of experience. Growing up in Toronto, he became an avid Maple Leafs and Blue Jays fan, but also admires the New York Islanders and Los Angeles Dodgers for their dominance in the 80s. Holding an Economics and Education major, Nestor’s passion for writing and sporting events led him to take up reporting about the sport professionally.

Nestor credits the Leafs’ playoff runs in the early ’90s as having a lasting impact on him. His favorite players are Doug Gilmour and Mike Bossy, as he feels they were tough, talented leaders, while Pat Burns is his favorite coach of all time for always preaching a fast-paced game.

Growing up in Canada, it was natural for Nestor to become interested in ice hockey and he played Minor Hockey as a teenager, which has given him a unique perspective on the sport. Nestor has mastered the art of how to best present facts and he also has a knack for knowing which sources can be trusted, and which can’t for stories.

When he is not writing about Canada’s national passion, Nestor enjoys running and hiking.

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Edited by Nestor Quixtan