O'Brien Trophy Winners
| Year |
Winner(s) |
| 1950 |
Montreal Canadiens |
| 1949 |
Boston Bruins |
| 1948 |
Detroit Red Wings |
| 1947 |
Toronto Maple Leafs |
| 1946 |
Boston Bruins |
| 1945 |
Detroit Red Wings |
| 1944 |
Detroit Red Wings |
| 1943 |
Boston Bruins |
| 1942 |
Toronto Maple Leafs |
| 1941 |
Toronto Maple Leafs |
| 1940 |
New York Rangers |
| 1939 |
New York Rangers |
| 1938 |
Toronto Maple Leafs |
| 1937 |
Montreal Canadiens |
| 1936 |
Montreal Maroons |
| 1935 |
Toronto Maple Leafs |
| 1934 |
Toronto Maple Leafs |
| 1933 |
Toronto Maple Leafs |
| 1932 |
Montreal Canadiens |
| 1931 |
Montreal Canadiens |
| 1930 |
Montreal Maroons |
| 1929 |
Montreal Canadiens |
| 1928 |
Montreal Canadiens |
| 1923 |
Ottawa Senators |
| 1922 |
Toronto St. Pats |
| 1921 |
Ottawa Senators |
| 1920 |
Ottawa Silver Seven |
| 1919 |
Montreal Canadiens |
| 1918 |
Toronto Arenas |
| 1917 |
Montreal Canadiens |
| 1916 |
Montreal Canadiens |
| 1915 |
Ottawa Senators |
| 1914 |
Toronto Blueshirts |
| 1913 |
Quebec Bulldogs |
| 1912 |
Quebec Bulldogs |
| 1911 |
Ottawa Senators |
| 1910 |
Montreal Wanderers |
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