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.
Mike Gartner, Luke Richardson and Harry Howell played well over 1400 games without winning a Cup. Many have played over 1000 games without winning. However, these guys at least made the playoffs once in a while. The most unusual is probably Guy Charron who played 734 regular season games with Montreal, Kansas City, Detroit and Washington and not only never won a Cup but never once made the playoffs.
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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.
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.
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.
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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.
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 Detroit Red Wings
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.
Daniel sedin or Ovechkin or stamkos