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The Stanley Cup is the championship trophy in the NHL
It is the oldest North American sports championship trophy (over 100 years)
The Stanley Cup is what every player dreams of winning in their career
| Season | Team | Coach |
| 1999-00 | New Jersey Devils | Larry Robinson |
| 1998-99 | Dallas Stars | Ken Hitchcock |
| 1997-98 | Detroit Red Wings | Scotty Bowman |
| 1996-97 | Detroit Red Wings | Scotty Bowman |
| 1995-96 | Colorado Avalanche | Marc Crawford |
| 1994-95 | New Jersey Devils | Jacques Lemaire |
| 1993-94 | New York Rangers | Mike Keenan |
| 1992-93 | Montreal Canadiens | |
| 1991-92 | Pittsburgh Penguins | Scotty Bowman |
| 1990-91 | Pittsburgh Penguins | Bob Johnson |
| 1989-90 | Edmonton Oilers | Glen Sather |
| 1988-89 | Calgary Flames | Terry Crisp |
| 1987-88 | Edmonton Oilers | Glen Sather |
| 1986-87 | Edmonton Oilers | Glen Sather |
| 1985-86 | Montreal Canadiens | Jean Perron |
| 1984-85 | Edmonton Oilers | Glen Sather |
| 1983-84 | Edmonton Oilers | Glen Sather |
| 1982-83 | New York Islanders | Al Arbour |
| 1981-82 | New York Islanders | Al Arbour |
| 1980-81 | New York Islanders | Al Arbour |
| 1979-80 | New York Islanders | Al Arbour |
| 1978-79 | Montreal Canadiens | Scotty Bowman |
| 1977-78 | Montreal Canadiens | Scotty Bowman |
| 1976-77 | Montreal Canadiens | Scotty Bowman |
| 1975-76 | Montreal Canadiens | Scotty Bowman |
| 1974-75 | Philadelphia Flyers | Fred Shero |
| 1973-74 | Philadelphia Flyers | Fred Shero |
| 1972-73 | Montreal Canadiens | Scotty Bowman |
| 1971-72 | Boston Bruins | Tom Johnson |
| 1970-71 | Montreal Canadiens | Al MacNeil |
| 1969-70 | Boston Bruins | Harry Sinden |
| 1968-69 | Montreal Canadiens | Claude Ruel |
| 1967-68 | Montreal Canadiens | Toe Blake |
| 1966-67 | Toronto Maple Leafs | Punch Imlach |
| 1965-66 | Montreal Canadiens | Toe Blake |
| 1964-65 | Montreal Canadiens | Toe Blake |
| 1963-64 | Toronto Maple Leafs | Punch Imlach |
| 1962-63 | Toronto Maple Leafs | Punch Imlach |
| 1961-62 | Toronto Maple Leafs | Punch Imlach |
| 1960-61 | Chicago Blackhawks | Rudy Pilous |
| 1959-60 | Montreal Canadiens | Toe Blake |
| 1958-59 | Montreal Canadiens | Toe Blake |
| 1957-58 | Montreal Canadiens | Toe Blake |
| 1956-57 | Montreal Canadiens | Toe Blake |
| 1955-56 | Montreal Canadiens | Toe Blake |
| 1954-55 | Detroit Red Wings | Jimmy Skinner |
| 1953-54 | Detroit Red Wings | Tommy Ivan |
| 1952-53 | Montreal Canadiens | Dick Irvin |
| 1951-52 | Detroit Red Wings | Tommy Ivan |
| 1950-51 | Toronto Maple Leafs | Joe Primeau |
| 1949-50 | Detroit Red Wings | Tommy Ivan |
| 1948-49 | Toronto Maple Leafs | Hap Day |
| 1947-48 | Toronto Maple Leafs | Hap Day |
| 1946-47 | Toronto Maple Leafs | Hap Day |
| 1945-46 | Montreal Canadiens | Dick Irvin |
| 1944-45 | Toronto Maple Leafs | Hap Day |
| 1943-44 | Montreal Canadiens | Dick Irvin |
| 1942-43 | Detroit Red Wings | Jack Adams |
| 1941-42 | Toronto Maple Leafs | Hap Day |
| 1940-41 | Boston Bruins | Cooney Weiland |
| 1939-40 | New York Rangers | Frank Boucher |
| 1938-39 | Boston Bruins | Art Ross |
| 1937-38 | Chicago Black Hawks | Bill Stewart |
| 1936-37 | Detroit Red Wings | Jack Adams |
| 1935-36 | Detroit Red Wings | Jack Adams |
| 1934-35 | Montreal Maroons | Tommy Gorman |
| 1933-34 | Chicago Black Hawks | Tommy Gorman |
| 1932-33 | New York Rangers | Lester Patrick |
| 1931-32 | Toronto Maple Leafs | Dick Irvin |
| 1930-31 | Montreal Canadiens | Cecil Hart |
| 1929-30 | Montreal Canadiens | Cecil Hart |
| 1928-29 | Boston Bruins | Cy Denney |
| 1927-28 | New York Rangers | Lester Patrick |
| 1926-27 | Ottawa Senators | Dave Gill |
| 1925-26 | Montreal Maroons | Eddie Gerard |
| 1924-25 | Victoria Cougars | Lester Patrick |
| 1923-24 | Montreal Canadiens | Leo Dandurand |
| 1922-23 | Ottawa Senators | Pete Green |
| 1921-22 | Toronto St. Pats | Eddie Powers |
| 1920-21 | Ottawa Senators | Pete Green |
| 1919-20 | Ottawa Senators | Pete Green |
| 1918-19 | No Series Because of Flu Epidemic | |
| 1917-18 | Toronto Arenas | Dick Carroll |
| 1916-17 | Seattle Metropolitans | Pete Muldoon |
| 1915-16 | Montreal Canadiens | George Kennedy |
| 1914-15 | Vancouver Millionaires | Frank Patrick |
| 1913-14 | Toronto Blue Shirts | Scotty Davidson |
| 1912-13 | Quebec Bulldogs | Joe Marlowe |
| 1911-12 | Quebec Bulldogs | Joe Marlowe |
| 1910-11 | Ottawa Senators | Bruce Stuart |
| 1909-10 | Montreal Wanderers | Pud Glass |
| 1908-09 | Ottawa Senators | Bruce Stuart |
| 1907-08 | Montreal Wanderers | Cecil Blachford |
| *1906-07 (January) | Montreal Wanderers | Cecil Blachford |
| *1906-07 (March) | Kenora Thistles | Tommy Phillips |
| 1905-06 | Montreal Wanderers | NA |
| 1904-05 | Ottawa Silver Seven | A. T. Smith |
| 1903-04 | Ottawa Silver Seven | A. T. Smith |
| 1902-03 | Ottawa Silver Seven | A. T. Smith |
| 1901-02 | Montreal A.A.A. | R. R. Boon |
| 1900-01 | Winnipeg Victorias | NA |
| 1899-1900 | Montreal Shamrocks | H. J. Trihey |
| 1898-99 | Montreal Shamrocks | H. J. Trihey |
| 1897-98 | Montreal Victorias | F. Richardson |
| 1896-97 | Montreal Victorias | Mike Grant |
| 1895-96 | Montreal Victorias | NA |
| 1894-95 | Montreal Victorias | Mike Grant |
| 1893-94 | Montreal A.A.A. | NA |
