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The Stanley cup first started in 1926 and was first awarded in 1927 and since then these teams have won, from the beginning:

Ottawa Senators

New York Rangers

Boston Bruins

Montreal Canadiens

Toronton Maple Leafs

Chicago Black Hawks

Montreal Maroons

Detroit Red Wings

Montreal Canadiens

Philadelphia Flyers

New York Islanders

Edmonton Oilers

Calgary Flames

Pittsburgh Penguins

New Jersey Devils

Colorado Avalanche

Dallas Stars

Tampa Bay Lightning

Carolina Hurricanes

Anaheim Ducks

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13y ago

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