The Montreal Canadiens with 24 (23 during the NHL era, and 1 win predates the NHL) are the winningest team in the NHL. The second most have been won by the Toronto Maple Leafs with 13, although they have not won since 1967.....
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The player with the most championships is Henri Richard who won 11 Cups with the Montreal Canadiens.
Wayne Gretzky has won the NHL MVP award (Hart Memorial Trophy) a record nine times during his career, eight consecutively.