1950
O'Brien Cup Champions
New York Rangers
1949
O'Brien Cup Champions
Montréal Canadiens
1948
O'Brien Cup Champions
Detroit Red Wings
1947
O'Brien Cup Champions
Montréal Canadiens
1946
O'Brien Cup Champions
Boston Bruins
1945
O'Brien Cup Champions
Detroit Red Wings
1944
O'Brien Cup Champions
Chicago Black Hawks
1943
O'Brien Cup Champions
Boston Bruins
1942
O'Brien Cup Champions
Detroit Red Wings
1941
O'Brien Cup Champions
Detroit Red Wings
1940
O'Brien Cup Champions
Toronto Maple Leafs
1939
O'Brien Cup Champions
Toronto Maple Leafs
1938
O'Brien Cup Champions
Toronto Maple Leafs
1937
O'Brien Cup Champions
Montréal Canadiens
1936
O'Brien Cup Champions
Montréal Maroons
1935
O'Brien Cup Champions
Toronto Maple Leafs
1934
O'Brien Cup Champions
Toronto Maple Leafs
1933
O'Brien Cup Champions
Toronto Maple Leafs
1932
O'Brien Cup Champions
Montréal Canadiens
1931
O'Brien Cup Champions
Montréal Canadiens
1930
O'Brien Cup Champions
Montréal Maroons
1929
O'Brien Cup Champions
Montréal Canadiens
1928
O'Brien Cup Champions
Montréal Canadiens
1927
O'Brien Cup Champions
Ottawa Senators
1926
O'Brien Cup Champions
Montréal Maroons
1925
O'Brien Cup Champions
Montréal Canadiens
1924
O'Brien Cup Champions
Montréal Canadiens
1923
O'Brien Cup Champions
Ottawa Senators
1922
O'Brien Cup Champions
Toronto St. Patricks
1921
O'Brien Cup Champions
Ottawa Senators
1920
O'Brien Cup Champions
Ottawa Senators
1919
O'Brien Cup Champions
Montréal Canadiens
1918
O'Brien Cup Champions
Toronto Hockey Club
