The Montreal Canadiens have won the most Stanley Cups with 24.
Montreal Canadiens have 23 Stanley Cups. Dave
the Toronto maple leafs won the second most Stanley cups!
Detroit Red Wings
The Boston Bruins with 6.
ken dryden.
No. Montreal has the most Stanley cup wins
The Montreal Canadiens currently lead in this category with 24 Cup wins.
Montreals canadians
Henri richard with 11 cups
The Montreal Canadiens have, at 24 times
The Montreal Canadiens, they have the most Stanley Cup wins