Detroit Redwings in 1997 and 1998.
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.
The last Canadian team to win the Stanley Cup was the Montreal Canadians, during the 1992,93 season.
36 years ago
Los Angeles Kings