Canada introduced hockey to the world, and it only makes sense that Canadian teams would typically dominate the NHL landscape. However, that has not been the case for nearly three decades.

The Montreal Canadiens last hoisted the Stanley Cup in the 1992-93 season. Over the past 30 years, it has been a painful drought for the country with seven teams in the league seeking to seize hockey’s most prized trophy again. Last season, the Edmonton Oilers approached closely after overcoming a 3-0 deficit but ultimately fell to the Florida Panthers in Game 7.

This season brings renewed hope with five Canadian teams in the playoffs, marking the highest representation since 2017.

So, which Canadian teams are best positioned to win the Stanley Cup this June? Here’s a closer look:

1. Toronto Maple Leafs

The Leafs have faced substantial postseason hurdles, eliminated in the first round seven times over the past eight years. Nevertheless, their front line boasts elite players like Auston Matthews, William Nylander, Mitch Marner, and John Tavares. Despite some weaknesses during five-on-five play, their power-play unit excels, converting at a 24.8% rate. They are set to meet the Senators, a series they could potentially win. However, the path to the Cup is complicated as they may confront the Lightning or Panthers thereafter.

2. Winnipeg Jets

The Jets achieved the Presidents’ Trophy for the first time this season, yet history weighs heavily—they are one of many top teams to struggle post-award. Their goaltender Connor Hellebuyck has faltered in playoffs past, with records indicating unpredictability. They face a challenging first round against the aggressive St. Louis Blues.

3. Edmonton Oilers

Fresh off a Stanley Cup Final near-miss in 2024, the Oilers retain a dynamic duo in Connor McDavid and Leon Draisaitl. However, injuries are stacking up, particularly to vital players, which could heavily impact their pursuit of the Cup.

4. Ottawa Senators

After a seven-year absence from playoffs, their young talent is finally making headway. They clash with the experienced Maple Leafs in the first round, which won’t be easy despite the promising future ahead for Ottawa.

5. Montreal Canadiens

The irony lies in the fact that while the Canadiens were the last Canadian champions, they appear the least likely to succeed now. They managed a playoff spot but meet a formidable Capitals team first round, making their road particularly daunting.

For more details on the NHL playoffs, check out CBS Sports’ extensive coverage.