Toronto has won more Stanley Cups, having won 13 Stanley Cups.The original Ottawa Senators have won the Stanley Cup 5 times, but the current Ottawa Senators have not yet won the Stanley cup.
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
The Canadians
Scotty Bowman
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.
ken dryden -6
ken dryden
Canadiens
Montreal Canadians with 24
Toronto
The Montreal Canadiens have won 24, which is the most by far.
Montreal Canadien won this and most Stanley cups.