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.
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The Montreal Canadiens have won the Stanley Cup 24 times.
If Canadians refers to teams from Canada, The Stanley cup has been won by Canadian teams a total of 51 times, including defunct teams.
The Ottawa Senators are one of the most historic and successful teams in the NHL. Prior to the 2014-2015 season, the team has won 7 Stanley Cups.
This depends on the cup and the sport. Please see related questions or re-ask your question.