Which Canadian Team Is Most Likely to Win Stanley Cup in 2027?

No Canadian team has shorter Stanley Cup odds at the BetMGM online sportsbook than the Edmonton Oilers.

With their new, formerly blacklisted head coach at the helm, can the Oilers get over the final hurdle, or does another Canadian team have a better shot at winning the Stanley Cup?

Which Canadian NHL Team Will Be the Best in 2027?

It’s now 33 seasons without a Canadian team winning the Stanley Cup. A Canadian team advanced to the Stanley Cup Final or the conference final in the previous three seasons, providing hope for the 2026-27 campaign. 

The Oilers’ odds to win the Stanley Cup carry an implied probability of 9.09%, and the Montreal Canadiens are the next closest at 4.76%. 

Between those teams, the Oilers represent the best bet. However, I’m going to wait to see how the team reacts to Babcock’s my-way-or-the-highway mantra. 

Hiring the ostracized coach could be crazy enough to work, given the leadership team’s full buy-in. Zach Hyman is one of the most outspoken proponents of Babcock, having played under the dogmatic coach during his previous reign with the Toronto Maple Leafs. 

The Canadiens will likely struggle to replicate last season’s success, especially with the Florida Panthers on the prowl after acquiring Brady Tkachuk. They will enter the regular season with the most stacked lineup, which includes the healthy Aleksander Barkov. 

The Ottawa Senators’ Stanley Cup odds took a significant hit after Tkachuk’s departure. While the team was left with no option but to trade Tkachuk, it could take some time to overcome the void he left in the lineup. 

Where Do the Toronto Maple Leafs Stand?

The Maple Leafs Stanley Cup odds are the fourth shortest. Their hockey odds improved from +6000 to +3500 after selecting Gavin McKenna first overall. 

General manager John Chayka isn’t wasting any time trying to get the team where he envisions it. He has already made multiple trades, one of which brought Darren Raddysh in from the Tampa Bay Lightning. 

He hired another ally in Jim Hiller. The Maple Leafs head coach is aligned with Chayka on the desire for a quicker, more puck-moving defence and a team that is comfortable in possession. 

While I can’t see the Maple Leafs overcoming the Carolina Hurricanes or Florida Panthers, they should get back to the postseason after missing out last year.

How About the Calgary Flames, Winnipeg Jets, and Vancouver Canucks? 

The Connor Hellebuyck rumours continue to emanate from Winnipeg, as Winnipeg Jets president and general manager Kevin Cheveldayoff entertains offers for the three-time Vezina Trophy winner. 

The Jets aren’t good enough to recapture their 2024-25 Presidents’ Trophy-winning form, but it should be a better campaign than the last, which saw them miss the playoffs for the first time in three seasons. 

Unless Hellebuyck is dealt, that is. 

The Flames have a lot to look forward to as general manager Craig Conroy continues to rebuild the roster expertly. 

They recently added the No. 2 pick from the 2022 draft, Šimon Nemec, to the roster, another step forward in rebuilding the blue line. On that note, the Flames secured high-scoring defenceman Carson Carels with the No. 6 pick in last week’s draft.  

Last season’s bottom-feeders, the Vancouver Canucks, are tied with the Calgary Flames for the least likely Canadian teams to obtain hockey’s ultimate prize. Their +50000 odds translate to a 0.20% probability. 

The Canucks selected Caleb Malhotra with the third-overall pick. Touted as the best centre in the recent draft, he’s the son of head coach Manny Malhotra. 

Stanley Cup Odds