Henri Richard, who played for the Montreal Canadiens, holds the record for winning the most Stanley Cups in NHL history, as of 2014. Richard won 11 total Stanley Cups in his 20-year career.
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The Montreal Canadiens won the Stanley Cup five times in a row in the 1960s. Runners up, like the Islanders, have won the Stanley cup four times in a row.
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Jean Beliveau has won 17 Stanley Cups. (10 as player, 7 as executive) Henri Richard has won 11 Stanley Cups, all as a player. The Montreal Canadiens have won the most Stanley …Cups with 24. The Montreal Canadiens have won the most Stanley Cups, as of 2014.
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According to the Pittsburgh Penguins' website, the team has won three Stanley Cup titles as of 2014. The Penguins' first championship occurred in the 1990-1991 season. They won their second championship in 1991-1992, and their latest championship occurred in 2008-2009.
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The Montreal Canadiens have won the Cup a record 24 times and are the most recent Canadian-based team to win the cup, having won it in 1993. The Stanley Cup was not awarded in 1919 because of a Spanish flu epidemic, and in 2005, as a consequence of the 2004–05 NHL lockout.
https://en.wikipedia.org/wiki/Stanley_Cup
Jean Beliveau is second on the record list with 10 Stanley Cup wins, which he also won while he was with the Montreal Canadiens. Richard and Beliveau played together on the Canadiens for 15 years, acquiring all of their championships together. Additionally, the Canadiens are the professional hockey team with the most Stanley Cup wins. The team has won Lord Stanley's Cup 23 times, 10 more than the next closest team, the Toronto Maple Leafs.
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The team with the second most Stanley Cups is the Detroit Red Wings, with 11,although they haven't won a championship since 2008 Detroit Red Wings - Second - 11 cup champion…ships. Toronto Maple Leafs - Third - 11 cup championships.
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Originally commissioned in 1892 as the Dominion Hockey Challenge Cup, the trophy is named for Lord Stanley of Preston, then–Governor General of Canada, who awarded it to Canada's top-ranking amateur ice hockey club, which the entire Stanley family supported, with the sons and daughters playing and promoting the game.
https://en.wikipedia.org/wiki/Stanley_Cup
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.
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On March 17, in the first ever Stanley Cup playoff game, the Montreal Hockey Club (Montreal HC) defeated the Montreal Victorias, 3–2. Five days later, in the first Stanley Cup Final game, Montreal HC beat the Ottawa Hockey Club 3–1.
https://en.wikipedia.org/wiki/Stanley_Cup
which team has the most stanley cups
The Montreal Canadiens  team has the most Stanley cups. The Montreal Canadiens have the most Stanley Cups.