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Wayne Gretzky, Mario Lemieux, Bobby Orr, Gordie Howe, and Maurice "Rocket" Richard.
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Earn +20 ptsQ: What are the top five players with most Stanley cups?
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Which players won the most Stanley cup?
Henri Richard of the montrea canadiens with 11 cups.
What player has won the second most Stanley cups?
Henri Richard of the Montreal Canadiens leads with 11 Stanley Cups as a player. Jean Beliveau and Yvan Cournoyer also of Montreal, have 10 cup wins each as players.
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