| Results |
| WINNERS PRIOR TO FORMATION OF NHL IN 1917 |
| Year |
Team |
|
1892-93 | Montreal A.A.A. |
|
1893-94
| Montreal
A.A.A. |
|
1894-95
| Montreal Victorias |
|
1895-96
| Winnipeg Victorias (Feb) |
|
1895-96
| Montreal Victorias (Dec) |
|
1896-97
| Montreal Victorias |
|
1897-98
| Montreal Victorias |
|
1898-99
| Montreal Victorias (Feb) |
|
1898-99
| Montreal Shamrocks (Mar) |
|
1899-1900
| Montreal Shamrocks |
|
1900-01
| Winnipeg Victorias |
|
1901-02
| Winnipeg Victorias (Jan) |
|
1901-02
| Montreal A.A.A. (Mar) |
|
1902-03
| Montreal A.A.A. (Feb) |
|
1902-03
| Ottawa Silver Seven (Mar) |
|
1903-04
| Ottawa Silver Seven |
|
1904-05
| Ottawa Silver Seven |
|
1905-06
| Ottawa Silver Seven (Feb) |
|
1905-06
| Montreal Wanderers (Mar) |
|
1906-07
| Kenora Thistles (Jan) |
|
1906-07
| Montreal Wanderers (Mar) |
|
1907-08
| Montreal Wanderers |
|
1908-09
| Ottawa Senators |
|
1909-10
| Montreal Wanderers |
|
1910-11
| Ottawa Senators |
|
1911-12
| Quebec Bulldogs |
|
1912-13
| Quebec Bulldogs |
|
1913-14
| Toronto Blueshirts |
|
1914-15
| Vancouver Millionaires |
|
1915-16
| Montreal Canadiens |
|
1916-17
| Seattle Metropolitans |
| NHL WINNERS AND FINALISTS |
| Season |
Champion |
Finalist |
GP in Final |
| 1917-18 | Toronto Arenas | Vancouver Millionaires | 5 |
| 1918-19 | No decision* | No decision* | 5 |
| 1919-20 | Ottawa Senators | Seattle Metropolitans | 5 |
| 1920-21 | Ottawa Senators | Vancouver Millionaires | 5 |
| 1921-22 | Toronto St Pats | Vancouver Millionaires | 5 |
| 1922-23 | Ottawa Senators | Vancouver Maroons,
Edmonton Eskimos | 2, 4 |
| 1923-24 | Montreal Canadiens | Vancouver Maroons,
Calgary Tigers | 2, 2 |
| 1924-25 | Victoria Cougars | Montreal Canadiens | 4 |
| 1925-26 | Montreal Maroons | Victoria Cougars | 4 |
| 1926-27 | Ottawa Senators | Boston Bruins | 4 |
| 1927-28 | New York Rangers | Montreal Maroons | 5 |
| 1928-29 | Boston Bruins | New York Rangers | 2 |
| 1929-30 | Montreal Canadiens | Boston Bruins | 2 |
| 1930-31 | Montreal Canadiens | Chicago Blackhawks | 5 |
| 1931-32 | Toronto Maple Leafs | New York Rangers | 3 |
| 1932-33 | New York Rangers | Toronto Maple Leafs | 4 |
| 1933-34 | Chicago Blackhawks | Detroit Red Wings | 4 |
| 1934-35 | Montreal Maroons | Toronto Maple Leafs | 3 |
| 1935-36 | Detroit Red Wings | Toronto Maple Leafs | 4 |
| 1936-37 | Detroit Red Wings | New York Rangers | 5 |
| 1937-38 | Chicago Blackhawks | Toronto Maple Leafs | 4 |
| 1938-39 | Boston Bruins | Toronto Maple Leafs | 5 |
| 1939-40 | New York Rangers | Toronto Maple Leafs | 6 |
| 1940-41 | Boston Bruins | Detroit Red Wings | 4 |
| 1941-42 | Toronto Maple Leafs | Detroit Red Wings | 7 |
| 1942-43 | Detroit Red Wings | Boston Bruins | 4 |
| 1943-44 | Montreal Canadiens | Chicago Blackhawks | 4 |
| 1944-45 | Toronto Maple Leafs | Detroit Red Wings | 7 |
| 1945-46 | Montreal Canadiens | Boston Bruins | |
| 1946-47 | Toronto Maple Leafs | Montreal Canadiens | 6 |
| 1947-48 | Toronto Maple Leafs | Detroit Red Wings | 4 |
| 1948-49 | Toronto Maple Leafs | Detroit Red Wings | 4 |
| 1949-50 | Detroit Red Wings | New York Rangers | 7 |
| 1950-51 | Toronto Maple Leafs | Montreal Canadiens | 5 |
| 1951-52 | Detroit Red Wings | Montreal Canadiens | 4 |
| 1952-53 | Montreal Canadiens | Boston Bruins | 5 |
| 1953-54 | Detroit Red Wings | Montreal Canadiens | 7 |
| 1954-55 | Detroit Red Wings | Montreal Canadiens | 7 |
| Season | Champion | Finalist | GP in Final |
| 1955-56 | Montreal Canadiens | Detroit Red Wings | 5 |
| 1956-57 | Montreal Canadiens | Boston Bruins | 5 |
| 1957-58 | Montreal Canadiens | Boston Bruins | 6 |
| 1958-59 | Montreal Canadiens | Toronto Maple Leafs | 5 |
| 1959-60 | Montreal Canadiens | Toronto Maple Leafs | 4 |
| 1960-61 | Chicago Blackhawks | Detroit Red Wings | 6 |
| 1961-62 | Toronto Maple Leafs | Chicago Blackhawks | 6 |
| 1962-63 | Toronto Maple Leafs | Detroit Red Wings | 5 |
| 1963-64 | Toronto Maple Leafs | Detroit Red Wings | 7 |
| 1964-65 | Montreal Canadiens | Chicago Blackhawks | 7 |
| 1965-66 | Montreal Canadiens | Detroit Red Wings | 6 |
| 1966-67 | Toronto Maple Leafs | Montreal Canadiens | 6 |
| 1967-68 | Montreal Canadiens | St Louis Blues | 4 |
| 1968-69 | Montreal Canadiens | St Louis Blues | 4 |
| 1969-70 | Boston Bruins | St Louis Blues | 4 |
| 1970-71 | Montreal Canadiens | Chicago Blackhawks | 7 |
| 1971-72 | Boston Bruins | New York Rangers | 6 |
| 1972-73 | Montreal Canadiens | Chicago Blackhawks | 6 |
| 1973-74 | Philadelphia Flyers | Boston Bruins | 6 |
| 1974-75 | Philadelphia Flyers | Buffalo Sabres | 6 |
| 1975-76 | Montreal Canadiens | Philadelphia Flyers | 4 |
| 1976-77 | Montreal Canadiens | Boston Bruins | 4 |
| 1977-78 | Montreal Canadiens | Boston Bruins | 6 |
| 1978-79 | Montreal Canadiens | New York Rangers | 5 |
| 1979-80 | New York Islanders | Philadelphia Flyers | 6 |
| 1980-81 | New York Islanders | Minnesota North Stars | 5 |
| 1981-82 | New York Islanders | Vancouver Canucks | 4 |
| 1982-83 | New York Islanders | Edmonton Oilers | 4 |
| 1983-84 | Edmonton Oilers | New York Islanders | 5 |
| 1984-85 | Edmonton Oilers | Philadelphia Flyers | 5 |
| 1985-86 | Montreal Canadiens | Calgary Flames | 6 |
| 1986-87 | Edmonton Oilers | Philadelphia Flyers | 7 |
| 1987-88 | Edmonton Oilers | Boston Bruins | 4 |
| 1988-89 | Calgary Flames | Montreal Canadiens | 6 |
| 1989-90 | Edmonton Oilers | Boston Bruins | 5 |
| 1990-91 | Pittsburgh Penguins | Minnesota North Stars | 6 |
| 1991-92 | Pittsburgh Penguins | Chicago Blackhawks | 4 |
| 1992-93 | Montreal Canadiens | Los Angeles Kings | 5 |
| 1993-94 | New York Rangers | Vancouver Canucks | 7 |
| 1994-95 | New Jersey Devils | Detroit Red Wings | 4 |
| 1995-96 | Colorado Avalanche | Florida Panthers | 4 |
| 1996-97 | Detroit Red Wings | Philadelphia Flyers | 4 |
| 1997-98 | Detroit Red Wings | Washington Capitals | 4 |
|
