The Toronto Maple Leafs own the second-most Stanley Cup titles in NHL history. But it’s been well over a half-century since their last championship triumph.
The Leafs saw their record Stanley Cup drought extended with a second-round loss to the defending champion Florida Panthers in the 2025 NHL playoffs.
Toronto, the Atlantic Division’s No. 1 seed, eliminated the wild-card Ottawa Senators in six games this postseason before jumping out to a 2-0 series lead over Florida. The Panthers then responded with three straight wins, but the Leafs won Game 6 on the road to keep their season alive.
But, in a decisive Game 7 at home, the Leafs were booed off the ice as an ugly 6-1 defeat pushed the storied franchise’s championship drought even closer to six decades.
When was the last time the Maple Leafs won the Stanley Cup?
The Leafs’ most recent Stanley Cup championship came in the 1966-67 season.
What’s the longest Stanley Cup drought in NHL history?
Toronto’s current championship drought is the longest in NHL history at 58 years.
The Buffalo Sabres and Vancouver Canucks both are mired in title droughts of 50-plus years, as well. Buffalo and Vancouver joined the NHL in the 1970-71 season and neither has won a Stanley Cup in the 54 years since. The Canucks have reached three Stanley Cup Finals (1982, 1994, 2011) and the Sabres have reached two (1975, 1999).
When was the last time the Maple Leafs made the Stanley Cup Final?
The Leafs’ 1966-67 championship campaign also stands as their last appearance in the Stanley Cup Final. That means the Original Six franchise hasn’t reached the Cup Final in the expansion era (since the 1967-68 season).
The Leafs last appeared in the conference final in the 2002 postseason.
How many Stanley Cup Finals have the Maple Leafs made?
Toronto has reached the Cup Final 21 times, trailing only the Montreal Canadiens (33 appearances) and Detroit Red Wings (24 appearances) for the most in NHL history.
How many Stanley Cups have the Maple Leafs won?
The Leafs were victorious in 13 of those 21 Cup Finals. Only the 23-time champion Canadiens have won more Stanley Cups than Toronto.
Here’s a full look at Toronto’s Stanley Cup Final history (years listed are when Cup Finals were played):
- 1967: Beat Montreal Canadiens
- 1964: Beat Detroit Red Wings
- 1963: Beat Detroit Red Wings
- 1962: Beat Chicago Blackhawks
- 1960: Lost to Montreal Canadiens
- 1959: Lost to Montreal Canadiens
- 1951: Beat Montreal Canadiens
- 1949: Beat Detroit Red Wings
- 1948: Beat Detroit Red Wings
- 1947: Beat Montreal Canadiens
- 1945: Beat Detroit Red Wings
- 1942: Beat Detroit Red Wings
- 1940: Lost to New York Rangers
- 1939: Lost to Boston Bruins
- 1938: Lost to Chicago Blackhawks
- 1936: Lost to Detroit Red Wings
- 1935: Lost to Montreal Maroons
- 1933: Lost to New York Rangers
- 1932: Beat New York Rangers
- 1922: Beat Vancouver Millionaires
- 1918: Beat Vancouver Millionaires
Editor’s note: This story was first published on April 21.
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