Detroit has won 11 Stanley Cup Championships. Pittsburgh has only won the Cup three times.
Detroit Red Wings, 11 Stanley Cups total from a early as 1935 and as recent as 2008.
The New York Islanders, who won Stanley Cups from 4 Stanley Cups from 1980 to 1983.
Bowman won 9 Stanley Cups between 1973 and 2002 as head coach of the Montreal Canadiens (1973, 1976, 1977, 1978, 1979), Pittsburgh Penguins (1992), and Detroit Red Wings (1997, 1998, 2002). He also was a front office member when the Penguins (1991), Red Wings (2008), and Chicago Blackhawks (2010) won Stanley Cups.
The franchise known today as the Toronto Maple Leafs won the Cup in 1918 as the Toronto Hockey Club (later engraved on the Stanley Cup as the Toronto Arenas in 1947), and in 1922 as the Toronto St. Patricks. As of 2017, they have won 11 more as the Maple Leafs.
Red Kelly won four times with Detroit and four more with Toronto.
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 Montreal Canadiens have won 24 Stanley Cups.
Montreal
Three. Two consecutive Stanley Cups in the 1990-1991 and 1991-1992 seasons as team captain of the Pittsburgh Penguins and one more in the 2008-2009 season as co-owner and chairman of the Penguins. Mario Lemieux is the one person to have his name on the Cup as a player and an owner.
As of 2012, the Maple Leafs have won 13 Stanley Cups and the Flyers have won 2.
A dynasty, in sports, generally refers to a team that has won numerous/consecutive championships within several years or a decade. There are no official requirements in terms of number of championships within any number of years, but the most well-known dynastiest in the history of the NHL are: -New York Islanders of the 1980s (four consecutive Stanley Cups from 1908-83) -Montreal Canadiens of the 1960s (Stanley Cups in 65, 66, 68, 69), 70s (four consecutive Cups from 1975-79) -Edmonton Oilers of the 1980s (Stanley Cups in 84, 85, 87, 88 and 90) More recently, the Detroit Red Wings won three Cups in five years (97, 98 and 02), but calling them a dynasty is borderline.
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