The team that has won the most Stanley cups is the Montreal Canadiens. They have won 24 championships in their history.
Boston Bruins (6)
The Montreal Canadians with 24 Cups. The team in second place is Toronto Maple Leafs with 13 Cups.
The Montreal Canadiens.
The Montreal Canadiens have won 24 Stanley Cups
The Montreal Canadiens have won 24 Stanley Cups.
Montreal Canadians due to the fact they won 24 Stanley Cups and are the team with the highest amount of Stanley Cups won. Secondly, it would be Washington Capitals. Big fan of Alexander Ovechkin & Mike Green.
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 New York Islanders, who won Stanley Cups from 4 Stanley Cups from 1980 to 1983.
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.
The Montreal Canadiens have won 24 Stanley Cups. The runners up, Detroit and Toronto, have each won 11.
The Canadians