6 Cups
1929, 1939, 1941, 1970, 1972 and 2011
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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 Bruins
Boston Bruins
The Boston Bruins won the 2011 Stanley Cup.
The Boston Bruins with 6.