5 out of the 7 canadian teams have one the cup.
The Edmonton Oilers, Montreal Canadiens, Toronto Maple Leafs, Calgary Flames, and the Ottawa Senators have all one the cup at least once. The Winnipeg Jets and The Vancouver Canucks have not one a cup but the Canucks have made it to the finals 3 times.
Edit: sorry about that I was misinformed the original Ottawa Senators won 11 cups.
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The Montreal Canadiens were the last Canadian team to win the Stanley Cup, beating the Los Angeles Kings in the 1992/93 playoffs.
The 1974-1975 Philadalphia Flyers were the last All Canadian born team to win the Stanley Cup.
As of 2010, the last team to win the Stanley Cup on home ice was the Anaheim Ducks, who won it in five games in 2007.
The last Canadian team to win the Stanley Cup were the Montreal Canadiens in 1993.