The last Canadian-based team to win the Stanley Cup was the Montreal Canadiens in 1993.
2011: Vancouver Canucks
The New York Islanders won 4 straight Stanley Cups (1980-1983). In 1984, they went back to the Stanley Cup Finals for the 5th straight time but ultimately lost to the Edmonton Oilers in 5 games. The Oilers had lost the Stanley Cup Finals to the Islanders in 1983.
As of yet, no Minnesota team has won a Stanley cup, however the North Stars made the Stanley cup final twice (in '81 and '91), only winning 1 total game in those two series.
36 years ago
Henri Richard with Montreal canadiens - 11 times
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If your asking which professional team holds the record for most championships, it would be the New York Yankees of the MLB with 26 World Series. They are closely followed by the Montreal Canadiens of the NHL with 24 Stanley Cups. ---- Real Madrid of La Liga has won 31 La Liga titles, 17 Copa del Rey titles, and 9 European Cups. They are, by far, the most successful football team of all time.
Montreal Canadiens - 24 Stanley cups. Last Time, 1993 against the Los Angles kings.
Once. With the Flames
The last Canadian-based team to win the Stanley Cup was the Montreal Canadiens in 1993.
That would be 1983, at the end of the run of 4 Stanley Cups in a row from 1980-1983.
Winnipeg has won the Stanley Cup 6 times. In each of the years 1896, 1901 and 1902 the Winnipeg Victorias won the cup twice. The Stanley Cup was a challenge cup in the earlier days.Neither incarnation of the Winnipeg Jets has won the Stanley Cup at this time, either as the Winnipeg Jets or their other team (Phoenix Coyotes and Atlanta Thrashers).
As of 2012, Montreal Canadiens have won it 25 times (one time was pre-NHL).
2011: Vancouver Canucks
The last Canadian team to win the Stanley Cup was the Montreal Canadians, during the 1992,93 season.
1] The Montreal Canadiens with 24 Stanley Cup Wins2nd is the Toronto Maple Leafs with 11 Stanley cup wins3rd is the Detroit Red Wings with 10.