The Montreal Canadiens won the most championships in the NHL.
Montreal canadians
Chicago blackhawks
Montreal Canadiens
The Montreal Canadians
The New York Rangers have won four Stanley Cup championships.
The player with the most championships is Henri Richard who won 11 Cups with the Montreal Canadiens.
Montreal Canadiens (24)
As of now, the Toronto Maple Leafs.
3, 1990-91,1991-92,2008-9
In Spain, Real Madrid have won 32 La Liga championships. In North America, the New York Yankees have won 27 MLB championships and the Montreal Canadiens have won 24 NHL championships.
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.....