The last time the Maple Leafs were in the Stanley Cup? The world was very different
The last time the Maple Leafs were in the Stanley Cup? The world was very different originally appeared on The Sporting News . Add The Sporting News as a Preferred Source by clicking here .
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. MORE: Alex Ovechkin snaps an unfathomable streak 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.