When was last time Maple Leafs made, won Stanley Cup Final? NBC Connecticut [Video]

The Toronto Maple Leafs own the second-most Stanley Cup titles in NHL history. But it’s been over a half-century since their last championship triumph.

Toronto in the 2025 NHL playoffs is looking to snap the longest Stanley Cup drought of all time at 57 years.

The Maple Leafs this season won the Atlantic Division with 108 points, finishing atop their division in a full regular season for the first time since 1999-2000. That set up a first-round Battle of Ontario, with the Leafs and Ottawa Senators meeting in the playoffs for the first time since 2004. Toronto jumped out to a 1-0 series lead over Ottawa on Sunday.

So, will this finally be the year that the Leafs bring Lord Stanley back to Toronto? As Auston Matthews, Mitch Marner and Co. attempt to end the franchise’s championship drought, here’s a look at the Leafs’ Stanley Cup history:

The Leafs’ most recent Stanley Cup …