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The last time the Toronto Maple Leafs won the Stanley Cup was also the same year that the Maple Leafs last played in the Stanley Cup championship series at all.
It's been a while.
Since then, the Leafs have often found a way to be one of the most disappointing teams in the NHL. That's certainly the case in the 2025-26 season.
After bringing back much of the same roster that impressed last regular season and looked rather formidable for a portion of the postseason, the Leafs haven't resembled a competitive group at all.
They've fallen off the table and are in such a tricky draft pick spot that they might not even get to keep their first-round pick for a talented 2026 draft class.
Yeah, it's been a rough few years. Well really, decades.
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When's the last time the Maple Leafs were in the Stanley Cup?
The last time the Maple Leafs were in the Stanley Cup Finals was also the last time they won it: 1967.
That's right. They haven't made it back in nearly 60 years.
Notable events since Maple Leafs last played for a Stanley Cup
This list could be immensely long, but we'll stick to some relevant stuff:
- Toronto got a baseball team, and that baseball team won two World Series, and then after a 32-year drought, made it back to the World Series and nearly won it again.
- Wayne Gretzky broke every conceivable hockey record, tried various leadership roles in the NHL, and is now on TV.
- Computers.
- Cell phones.
- A World Cup is coming (partially) to Canada.
Get the idea?
Yeah, it's been a long, long time.
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