The Pittsburgh Penguins won the Stanley Cup in 2009
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The Montreal Canadiens have won 24 Stanley Cups.
The following Canadian NHL teams have won the Stanley Cup:Montreal CanadiensToronto Maple LeafsEdmonton OilersCalgary FlamesOlder teams:Ottawa Senators (not current expansion team)Montreal MaroonsVancouver MillionairesVictoria CougarsEdmonton EskimosCalgary Tigers
The Pittsburgh Penguins! They won it
They won the cup in 2009, 1992 and 1991
The team that has won the most Stanley cups is the Montreal Canadiens. They have won 24 championships in their history.