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.
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The team that has won the most Stanley cups is the Montreal Canadiens. They have won 24 championships in their history.
Italy come second after Brazil, with 4 world cups.
the canadiens are first with 24. then the leafs with 13, the red wings with 10, and after that, the Boston bruins and the Edmonton oilers have 5, and several more teams are just behind this with 4. so to answer your question, the Boston Bruins have won the second most Stanley cups of all American teams, with 5.
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.