Stanley Cup – 1931
The 1931 Stanley Cup Finals was played between the Montreal Canadiens and the Chicago Black Hawks, making their first Stanley Cup final appearance. The Canadiens, defending champions won the series to become the second NHL team to repeat as champion.

Stanley Cup – 1930
The 1930 Stanley Cup Final championship series was played between the Boston Bruins and the Montreal Canadiens. In a best of three series, Montreal won 4–3 and 3–0 to win the team’s third Stanley Cup championship.

Stanley Cup – 1924
The 1924 Stanley Cup Final saw the National Hockey League (NHL) champion Montreal Canadiens defeat the Western Canada Hockey League (WCHL) champion Calgary Tigers two games to none in the best-of-three game series. It was Montreal’s fourth appearance in the Final and second championship.

Stanley Cup – 1916
The 1916 Stanley Cup Final was played between the National Hockey Association (NHA) champion Montreal Canadiens and the Pacific Coast Hockey Association (PCHA) champion Portland Rosebuds. This was the first time that a best-of-five Cup championship went the distance. Also, the Rosebuds were the first team based in the United States to play for the Cup. The Canadiens defeated the Rosebuds three games to two in the best-of-five game series. This would be the first of 24 Stanley Cup championships for the Canadiens.