Which Canadian Team Is Most Likely to Win the Stanley Cup?

Three Canadian teams are in the running to qualify for the 2025-26 playoffs, but it will likely go down to the wire for the Ottawa Senators. The Montreal Canadiens are in a stable spot, and the Edmonton Oilers should be safe in the lacklustre Pacific Division. 

But which Canadian team is most likely to win the Stanley Cup and end the country’s 33-year drought?

Which Canadian NHL Team Will Go the Furthest in 2026?

Edmonton Oilers

With the shortest Stanley Cup odds among Canadian teams, the Oilers have the best chance to make a deep playoff run despite their tragically poor season.

The reason is two-fold: Connor McDavid is the best hockey player in the world, though Nikita Kucherov also states a compelling case. McDavid always saves his best for the postseason, a scary proposition for any forthcoming opponent. 

The Oilers are renowned for turning it on in the playoffs. While the likelihood of that occurring has diminished after an insipid season, there is still a chance. 

The only reason I’m giving them the benefit of the doubt is their recent playoff runs, which have seen them make consecutive Stanley Cup Finals.

Wouldn’t it, in the most ironic Oilers way, be fitting for them to get hot when it matters most? Just because we haven’t seen it this season doesn’t mean they aren’t capable.

That said, I don’t expect the Oilers to advance to their third straight final.

Montreal Canadiens

The Canadiens are a superb team and should be Stanley Cup contenders for years to come at the BetMGM online sportsbook. 

However, the collective hasn’t matured enough to make a deep playoff run, especially with a first-round matchup
against the Tampa Bay Lightning potentially looming.  

I’m also concerned with the Canadiens’ goaltending, with starter Jakub Dobeš sporting a 2.88 goals-against average and a subpar .896 save percentage. The 24-year-old has only two playoff starts under his belt, another reason to temper expectations. 

If they face the Buffalo Sabres in the first round, I expect the Canadiens to pull off the upset, but a matchup against the Lightning won’t go well.

Ottawa Senators

If the Senators make the playoffs, they could do some damage. That’s what I would have said before Thomas Chabot, the team’s No. 2 defenceman, went down with what will likely be a season-ending injury. 

The best-case scenario for his return is four weeks, which would take us to the second round of the playoffs. Six to eight weeks feels more realistic, though. 

Chabot averages 22:34 of ice time per game, the second-most behind Jake Sanderson (24:49). Speaking of Sanderson, he has been sidelined with an injury since March 7, but is expected to return imminently.

The Sens have the second-best record since Jan. 26 (14-3-3). They were my dark horse pick before the season started to make a deep run, but I’m unconvinced they can overcome the loss of Chabot.