The Montreal Canadiens won the Stanley Cup 5 times in the 1950s, in 53, 56, 57, 58, and 59,
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24 Stanley cups so far.
Four. Two with the Canadiens (1986, 1993) and two with the Avalanche (1996, 2001).
6 - Vancouver Canucks, Edmonton Oilers, Calgary Flames, Toronto Maple Leafs, Ottawa Senators, and Montreal Canadiens
4: John Ross Roach, Toronto St. Patricks, 1924-25. George Hainsworth, Montreal Canadiens, 1932-33. Charlie Gardiner, Chicago Black Hawks, 1933-34. Bill Durnan, Montreal Canadiens, 1947-48. After 1950, no goalies were captain because it was banned.