Edmonton Oilers

Hope For Stanley Cup: Oilers or Canadiens?

Discover the playoff hopes of the Oilers and Canadiens. Can Edmonton’s talent or Montreal’s youth triumph this season?

by
Garit Reid
March 22, 2026

If the playoffs started today, the hope for a Canadian Stanley Cup is between the Edmonton Oilers and Montreal Canadiens. For most, it seems, Connor McDavid and the Oilers are destined to win a Cup, but they have been thwarted in back-to-back Stanley Cup Finals losses. The Canadiens seem to be the dark horse with their young talent, but goaltending is their Achilles heel.

Does either team have a legitimate shot this season?

Third Time Is A Charm Unlikely For Oilers

For the Oilers to make the Stanley Cup Finals for a third consecutive year may prove difficult for McDavid, Leon Draisaitl, and the team. The Oilers obviously have the talent, but the law of probability will make it a challenge for them.

McDavid is too talented to not win a Stanley Cup in his career, the question is; will he do it with the Oilers?

Connor McDavid Oilers media — Edmonton Oilers’ player Connor McDavid

This season, it certainly doesn’t look like it. He acknowledged that the Pacific Division is a “pillow fight,” with every team losing, giving the impression that the Oilers might be worse than they appear. They haven’t lost ground in the standings, simply because no one has taken it.

Hope For The Habs

Cole Caufield is scoring in bunches this season, and with a hat-trick against the New York Islanders last night. The Canadiens are on the right track heading towards a playoff spot. The Habs will have to go on a hot streak if they have a chance of making the Stanley Cup Finals. Montreal’s goalie, Jakub Dobes, will have to stand on his head throughout the playoffs if there is any hope for a Stanley Cup.

Jakub Dobes Canadiens loss — Montreal Canadiens goaltender Jakub Dobes

Path To Lord Stanley North Of The Border

The key way the Oilers or Canadiens, or any team, wins a Stanley Cup in the playoffs can be summed up in one word: Overtime. For any team, skill, strong goaltending, and luck win a team, Lord Stanley. Luck comes in the form of winning more overtime games in the playoffs than any other team.

The last Canadian team to win the Stanley Cup was the Montreal Canadiens in 1993. They still own the record for most NHL playoff overtime wins in a single year, going 10-1.