The Toronto Maple Leafs last won the Stanley Cup in 1967. That was 58 years ago, making it the longest championship drought in the NHL at the moment.

For context, the average price of gas was $0.33 per gallon in the United States, while the hottest single was “To Sir with Love” by Lulu. The Beatles were still together and Lyndon B. Johnson was President.

That year, the Maple Leafs won the Cup in the league’s final season as an Original Six league. The NHL had agreed to double the size of the league, adding six new teams for the 1967-68 season: The Los Angeles Kings, Minnesota North Stars, Oakland Seals, Philadelphia Flyers, Pittsburgh Penguins, and St. Louis Blues.

Since that expansion, the Leafs have never been back to the Stanley Cup Final. The team had historically bad seasons while coming close a few times to making it back. But interestingly enough, the last time the Leafs won the Cup, the Boston Bruins and Detroit Red Wings didn’t qualify for the playoffs.

Under the pre-expansion rules, there were only two rounds. In the first round, the Leafs defeated the Chicago Blackhawks and the Montreal Canadiens bounced the New York Rangers. That set up a Leafs-Canadiens final for the Cup. The Leafs won the series 4-2.

1967 Stanley Cup: Toronto Vs. Montreal - Source: Getty
1967 Stanley Cup: Toronto Vs. Montreal – Source: Getty

The victory was Toronto’s 13th in the pre-expansion era and would be the last time. Considering that this season, both the Boston Bruins and Detroit Red Wings failed to make the playoffs in the same season for the first time since 1967, could history repeat itself?

There’s a good chance it could. With Auston Matthews and Mitch Marner leading the way, the Leafs have as good a chance as they’ve ever had.

Looking at the Toronto Maple Leafs path to the Stanley Cup

The last time the Maple Leafs won the cup, there were only two rounds of playoffs. This time around, the Leafs will need to get past four rounds to win the 2025 NHL playoffs.

The Leafs’ first-round opponent looks to be the Ottawa Senators. The Sens swept the season series this year, but Toronto has been historically successful against the Senators in the postseason.

Assuming the Leafs get past the Senators, they’ll meet the winner of the Tampa Bay Lightning and Florida Panthers first-round series. Both clubs are excellent and will have one of the best matchups in the Eastern Conference. It’s hard to pick a winner so let’s give the nod to the defending Stanley Cup champions.

That situation would set up a Leafs-Panthers second-round series. The Panthers bounced the Leafs in five games in 2023 after Toronto beat the Lightning in the first round that year. But again, let’s assume the Leafs get out of the second round, that would put them in the Conference Final for the first time since 2002.

Mats Sundin, who captained the Maple Leafs to their last Conference Final appearance, is featured in the team's Legends Row - Source: Imagn
Mats Sundin, who captained the Maple Leafs to their last Conference Final appearance, is featured in the team’s Legends Row – Source: Imagn

In the Conference Final, the Leafs would face the winner of the Metro Division bracket. Considering the Washington Capitals are the Metro’s best team this season, the Leafs could run into the NHL’s all-time leading goal-scorer in the Eastern Conference Final.

If the Leafs manage to get to the Stanley Cup Final, it’s anyone’s guess who could make it out of the Western Conference side of the bracket. The West’s representative could feature a team like the Winnipeg Jets, Dallas Stars, Colorado Avalanche, or Edmonton Oilers.

Ultimately, the Maple Leafs’ path to the Stanley Cup will be much harder than it was in 1967. But it seems like this year’s Leafs iteration could have the team’s best chance ever to bring home its 14th Stanley Cup.