Which Canadian NHL Teams Are Closest to Winning the Stanley Cup?

The NHL offseason is in full swing, and teams are making moves in preparation for next season. This article focuses on the seven Canadian teams and how close they are to competing for the Stanley Cup.

The Canadian teams can be labelled into three categories. There are two rebuilding teams, three middling or fringe playoff teams, and two contenders. A Canadian team hasn’t won the Stanley Cup since the 1993 Montreal Canadiens, so who will break that drought? Let’s rank all seven teams and take a look at who’s the closest to accomplishing that goal.

Seventh: Vancouver Canucks

The Vancouver Canucks are the furthest away from winning the Stanley Cup, and it’s not particularly close. They are two seasons removed from winning the Pacific Division before ultimately losing in Round 2 in a heartbreaking Game 7. Unfortunately, it’s been all downhill from there.

They lost their captain and franchise defenceman Quinn Hughes, who was traded to the Minnesota Wild last season. Their number-one goaltender, Thatcher Demko, inked a three-year contract extension beginning this season with an $8.5 million cap hit, but he hasn’t been able to stay healthy for his entire career. They’re also paying their underperforming number-one centre, Elias Pettersson, $11.6 million until 2032. It’s a messy situation in Vancouver.

Despite finishing last in the league, Vancouver didn’t win the draft lottery. They had the third overall pick in the 2026 draft and selected Caleb Malhotra, the son of new Canucks’ head coach Manny Malhotra. It will be interesting to see how that father-son dynamic works at the NHL level. The Canucks are in a rebuild, and it will be a few seasons before they even compete for a playoff spot, let alone be a Stanley Cup contender.

Sixth: Calgary Flames

There are only two Canadian teams truly in a rebuild, and the Calgary Flames are one of them. They are a lot further along than the Canucks. They have made good decisions as a franchise and drafted well. They lost their best players in Johnny Gaudreau and Matthew Tkachuk, which ultimately forced them into a rebuild.

The Flames are building a solid foundation, starting with the back end. They have their 25-year-old number-one netminder, Dustin Wolf, locked up for seven more seasons with a $7.5 million cap hit. They also have 20-year-old Zayne Parekh and 2026 sixth overall pick Carson Carels to build around. Then, they acquired 22-year-old Simon Nemec from the New Jersey Devils to add even more youth to the defence core.

However, their forward group is underwhelming. They don’t have that true elite forward to lead the offensive charge. The Flames will likely struggle to score goals. They were last in the league in goals per game last season with 2.54, and they didn’t add any impactful forwards to change that. Jonathan Huberdeau is still under contract for five more seasons with a hefty $10.5 million cap hit. Connor Zary has also been involved in trade rumours. If they move Zary, their offence will be even worse. Over the next three drafts, they have nine picks within the first two rounds. They must start drafting forwards in the first round. Calgary is still a few years away from competing for a playoff spot, and the fans must be patient.

Fifth: Winnipeg Jets

The Winnipeg Jets are in a weird spot. They’re one season removed from winning the Presidents’ Trophy, but they had an awful 2025-26 campaign. They missed the playoffs and finished seventh in the Central Division. They haven’t been able to go on deep runs with their current core and have only advanced to the Western Conference Final once this century, in 2018, and have no Stanley Cup Final appearances. Plus, they are in a challenging division, competing against the Colorado Avalanche, Dallas Stars, Minnesota Wild, and the up-and-coming Utah Mammoth.

They have a few elite players in Mark Scheifele, Kyle Connor and Josh Morrissey, but don’t have enough depth to push them over the edge. They will always be in the conversation when they have Connor Hellebuyck between the pipes, since he’s the best goalie in the league. However, the American netminder has been involved in trade rumours this offseason, so his future is uncertain. If the Jets lose Hellebuyck, they will be far away from competing for a championship.

Fourth: Ottawa Senators

The Ottawa Senators made the playoffs in back-to-back seasons after a seven-year playoff drought. Unfortunately, they had consecutive first-round exits. They’ve posted a 2-8 playoff record over the past two seasons, including a four-game sweep by the Carolina Hurricanes last season.

The Senators traded their captain, Brady Tkachuk, to the Florida Panthers for future assets. They also acquired William Eklund from the San Jose Sharks. Unfortunately, Tkachuk’s presence can’t be replaced. They have yet to win a playoff series with this current core, and without their former captain, getting over the hump becomes even more challenging.

Ottawa still has solid pieces, especially up front with Eklund, Tim Stützle, Drake Batherson, Dylan Cozens, Shane Pinto, Ridly Greig, and Fabian Zetterlund. Unfortunately, they have just over $5 million in cap space and have too many holes to fill. They will have a hard time competing in the competitive Atlantic Division with the Canadiens, Florida Panthers, Tampa Bay Lightning, Boston Bruins, Buffalo Sabres, and Toronto Maple Leafs battling for seeding.

Third: Toronto Maple Leafs

After missing the playoffs for the first time in nine seasons, the Maple Leafs won the draft lottery and selected Gavin McKenna first overall. Last season was an outlier, and they should be competitive in 2025-26.

Their core has remained intact with Auston Matthews, William Nylander, Matthew Knies, and John Tavares still on the team. Then, when you add youngsters McKenna and Easton Cowan, that’s a solid nucleus of young talent to build around.

They also signed the best free-agent defenceman on the market in Darren Raddysh. However, their blue line remains a weak point, and it will worsen once they trade Morgan Reilly. Their defensive core is aging, with six of them over 30. Four of those six are signed for four more seasons. Plus, they are currently $2.7 million over the salary cap. They have no wiggle room and need to make more changes before training camp.

Second: Edmonton Oilers

There’s a massive gap on this list between second and third. The Edmonton Oilers are second because any team with Connor McDavid and Leon Draisaitl have a chance to win the Cup. They made back-to-back Stanley Cup Final appearances in 2024 and 2025. So, they have been the closest team, but is their window closing?

The Oilers have arguably been the busiest team this offseason after a disappointing first-round exit. They fired head coach Kris Knoblauch and replaced him with Mike Babcock in a controversial decision. They also traded Darnell Nurse’s entire $9.25 million contract and acquired a young defenceman in the deal. They also signed Ryan Shea to replace Nurse and found a new-look defence core. Defence and goaltending have been their biggest priority, and it looks like they are trending in the right direction and addressing their issues.

They solidified their goaltending by acquiring 24-year-old Devon Levi and signing veteran Frederik Andersen to play alongside Tristan Jarry. They have three capable goalies, but that also comes with risk given Levi’s inexperience and Andersen’s health.

However, there’s still plenty of uncertainty. The core is getting older, and they’ve battled injuries during the last two playoff runs. Plus, Babcock hasn’t coached in the league since 2019. Is he still a good coach in 2026? Only time will tell. If this season doesn’t go well, the McDavid era might be over. The Oilers are under a ton of pressure to win this season, and if they don’t, tough decisions need to be made. This season could be all or nothing.

First: Montreal Canadiens

There’s an incredibly thin margin between first and second. While the Oilers are under pressure to win a championship this season, the Canadiens are built to go on deep runs every year, which is why they’re first.

They got a taste of the Eastern Conference Final last season and should be poised to repeat it. They have a young core that’s all signed long term. Nick Suzuki, Cole Caufield, and Juraj Slafkovský are all signed for under $8 million each until at least 2031, with Slafkovský signed until 2033. 20-year-old Ivan Demidov also signed an eight-year deal with a $9.15 million cap hit. Plus, they have two elite defencemen, Noah Dobson and Lane Hutson, signed until at least 2033. They also have 25-year-old Jakub Dobes in goal until 2031.

Montreal has just over $14.2 million in cap space. They also have a bunch of draft capital, including their first- and second-round picks in the next three drafts. They also have a third-round pick in 2028 and 2029. Therefore, they have the assets to acquire an impactful player to push them over the edge. The Canadiens are the best-positioned Canadian team to win the Stanley Cup now and in the future.

Who will finally break Canada’s Stanley Cup drought? Keep following The Hockey Writers for all your NHL content throughout the offseason.