Detroit Red Wings, 11 Stanley Cups total from a early as 1935 and as recent as 2008.
Strictly speaking, Toronto has won more Stanley Cups, having won the Stanley Cup when it was a challenge cup before the formation of the NHL. The Detroit Red Wings have won 13 Stanley Cups, while the number of Stanley Cups the Toronto Maple Leafs have won is disputed. They have won 11 Stanley Cups as the Maple Leafs, but also won 1 as the St. Patricks, and 1 as the Arenas before that, both precursors to the Maple Leafs. Before that, the Toronto Hockey Club won the Stanley Cup as a challenge cup.
This depends on if you count all 13 of the Maple Leafs' Stanley Cups. The Detroit Red Wings have won 11 Stanley Cups. The Toronto Maple Leafs have won 13 Stanley Cups: 11 as the Toronto Maple Leafs, and one each as the Toronto Arenas and the Toronto St. Patricks. The name was changed from Arenas to St. Patricks in 1919 and from the St. Patricks to the Maple Leafs in 1927.
The team who won the more Stanley Cups is Canadiens of Montreal, they had won 24 Stanley Cups, but unfortunately the last Stanley Cup was in 1993!
The New York Islanders, who won Stanley Cups from 4 Stanley Cups from 1980 to 1983.
Red Kelly won four times with Detroit and four more with Toronto.
The Montreal Canadiens have won more Stanley Cups than any other.As of the start of the 2010-2011 season, Montreal has won 25 Cups (one won pre-NHL era), Toronto has won 13, and Detroit Red Wings have won 11.Montreal Canadiennes.
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.
The Montreal Canadiens have won 24 Stanley Cups.
Maurice has 8 cups with the habs and Henri has 11!
According to NHL.com's Stanley Cup Record Book & History web page, Scotty Bowman has won more Stanley Cups than any other coach with a total of 9 championships. One more than Toe Blake who won 8 Cups as a coach. Contributed by Kevin H. Bugg, DC " Go Leafs! "