No, the Montreal Canadiens did not win in 2008.
Montreal
The Philadelphia Flyers beat the Boston Bruins 4 games to 2 in 1974 to win the Stanley Cup.
Montreal Canadiens
The Montreal Canadiens won their first Stanley Cup in 1916.
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The Montreal Amateur Athletic Association, affiliated with the Montreal HC (Hockey Club) was the first team to win the Stanley Cup in 1893.
The Montreal Canadiens in 1989.
Montreal Canadiens
Calgary Flames
The Montreal Canadiens
The last Canadian team to win the Stanley Cup was the Montreal Canadians, during the 1992,93 season.