The Toronto Maple Leafs have lost in the Stanley Cup Finals 8 times. Both the Montreal Canadiens and the Philadelphia Flyers have lost 6 times.
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
Red Kelly is the most successful NHL player who never played for Montreal. He won 8 Stanley Cups with Detroit and Toronto between 1950 and 1967.
THE TORONTO MAPLE LEAFS 13
The team with the second most Stanley Cups is the Detroit Red Wings, with 11,although they haven't won a championship since 2008 Detroit Red Wings - Second - 11 cup championships. Toronto Maple Leafs - Third - 11 cup championships.
The Montreal Canadiens is the only team in NHL history to have won 5 Stanley Cups in a row. They accomplished that feat between 1956 and 1960 inclusively. They also won 4 straight cups from 1976 to 1979. Other streaks worth noting are the NY Islanders who won 4 cups in a row from 1980 to 1983. The Edmonton Oilers won 4 in 5 years (1984, 1985, 1987, 1988)The Montreal Canadiens from 1956 to 1960, winning 5 Stanley Cups.
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
Scotty Bowman
The Canadians
Canadiens
ken dryden -6
Montreal Canadians with 24
Toronto
ken dryden
The Montreal Canadiens have won 24, which is the most by far.
Montreal Canadien won this and most Stanley cups.
No, the Montreal Canadiens have won the most Stanley Cups.
Yep