Maple Leafs hire Sundin, Chayka to lead front office
Toronto Maple Leafs appoint Mats Sundin and John Chayka to lead front office
The Montreal Canadiens have won more Stanley Cups than any other NHL team. Their storied franchise continues to hold the record for the most championships in the league's history.

How many Stanley Cups have the Montreal Canadiens won? History of this NHL original six franchise originally appeared on The Sporting News. Add The Sporting News as a Preferred Source by clicking here.
The Montreal Canadiens are as storied a franchise as you'll find in the National Hockey League.
They have won more Stanley Cups than any team in the history of the sport, and even though it's been a while, that's a mark they seem likely to retain.
They'd certainly like the chance to add to this record sooner rather than later.
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Montreal has 24 Stanley Cup championships all time.
Technically, 23 of those came in the NHL. The first came in 1916, when they played in the NHA before this current league was founded.
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The Montreal Canadiens have won a total of 24 Stanley Cups, the most in NHL history.
The last time the Montreal Canadiens won the Stanley Cup was in 1993.
The Montreal Canadiens are considered a storied franchise due to their rich history, numerous championships, and being one of the original six teams in the NHL.
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These are the years they hoisted the Cup:
They won those five titles in a row from 1956-60, something that seems unlikely to be matched.
Entering the 2026 postseason, the Canadiens last won the Cup in 1993.
It's the longest drought in franchise history, and they're trying to end it.