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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Manny Ramirez has the most postseason games played as a non-member of the Yankees. He played in 111 games.
The St. Louis Blues have won 138 playoff games and have never won a Stanley Cup. They've also PLAYED the most playoff games - 307 - without winning a Cup. The San Jose Sharks have played the most playoff games - 136 - and won the most - 64 - without even MAKING it to the final series. Of the NHL's 30 teams, 13 have never won a Cup, and 6 have never played in a final series. All that information comes from the NHL Guide and Record Book, issued every autumn and available in bookstores near you.
Red Kelly is the most successful NHL player who never played for Montreal. He won 8 Stanley Cups with Detroit and Toronto between 1950 and 1967.
Wayne Primeau who has played 90 games in the playoffs but has won no Stanley Cups. Miikka Kiprusoff and Jarome Iginla have both played 47 playoff games for the Flames.
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Most recently, in the 2013 Stanley Cup Playoffs, the Chicago Blackhawks won the Stanley Cup, beating the Boston Bruins in 6 games.
Accrington Stanley
The first year the Chicago Blachawks won the Stanley Cup, they beat the Detriot Red Wings. They won three out of the four games they played. Four years they won the Stanley Cup again, in 1938, they were able to beat the Toronto Maple Leafs, by winning three out of the four they played. Then next time they won the Cup was in 1961, when they beat the Detriot Red Wings, by winning 4 out of they six games they played. The third time the hawks took the cup was in 2010. They played the Philadelphia Flyer and beat them by winning four of the six games they played. The most recent Stanley Cup they won was in 2013, when the Hawks took the victory over Boston Bruins in a four to two game series.
the Detroit Red Wings
Daniel sedin or Ovechkin or stamkos
Since the true beginning of the Stanley Cup in 1927; The Eastern conference has won 60 of the Stanley cup games, and the Western Conference has won 25. Hope this helps.