The Stanley Cup, which was donated by Frederick Arthur, Lord Stanley of Preston, and son of the Earl of Derby in 1893, is the oldest trophy competed for by professional athletes in North America.
Lord Stanley purchased the trophy for 10 pounds ($48.67 at the time) for presentation to the amateur hockey champions of Canada. It has been competed for, and only by NHL teams since 1926.
STANLEY CUP WINNERS PRIOR TO FORMATION OF N.H.L IN 1917
1895-1896 Winnipeg Victorias
1896-1897 Montreal Victorias
1897-1898 Montreal Victorias
1898-1899 Montreal Victorias
1899-1900 Montreal Shamrocks
1900-1901 Winnipeg Victorias
1901-1902 Montreal A. A. A.
1902-1903 Ottawa Silver Seven
1903-1904 Ottawa Silver Seven
1904-1905 Ottawa Silver Seven
1905-1906 Montreal Wanderers
1906-1907 Kenora Thistles
1907-1908 Montreal Wanderers
1908-1909 Ottawa Senators
1909-1910 Ottawa Senators
1910-1911 Ottawa Senators
1911-1912 Quebec Bulldogs
1912-1913 Quebec Bulldogs
1913-1914 Toronto Arenas
1914-1915 Vancouver Millionaires
1915-1916 Montreal Canadiens
1916-1917 Seattle Metropolitans
1917-1918 Toronto Arenas
1918-1919 No Winner
1919-1920 Ottawa Senators
1920-1921 Ottawa Senators
1921-1922 Toronto St. Patricks
1922-1923 Ottawa Senators
1923-1924 Montreal Canadiens
1924-1925 Victoria Cougars
1925-1926 Montreal Maroons
1926-1927 Ottawa Senators
1927-1928 New York Rangers
1928-1929 Boston Bruins
1929-1930 Montreal Canadiens
1930-1931 Montreal Canadiens
1931-1932 Toronto Maple Leafs
1932-1933 New York Rangers
1933-1934 Chicago Black Hawks
1934-1935 Montreal Maroons
1935-1936 Detroit Red Wings
1936-1937 Detroit Red Wings
1937-1938 Chicago Black Hawks
1938-1939 Boston Bruins
1939-1940 New York Rangers
1940-1941 Boston Bruins
1941-1942 Toronto Maple Leafs
1942-1943 Detroit Red Wings
1943-1944 Montreal Canadiens
1944-1945 Toronto Maple Leafs
1945-1946 Montreal Canadiens
1946-1947 Toronto Maple Leafs
1947-1948 Toronto Maple Leafs
1948-1949 Toronto Maple Leafs
1949-1950 Detroit Red Wings
1950-1951 Toronto Maple Leafs
1951-1952 Detroit Red Wings
1952-1953 Montreal Canadiens
1953-1954 Detroit Red Wings
1954-1955 Detroit Red Wings
1955-1956 Montreal Canadiens
1956-1957 Montreal Canadiens
1957-1958 Montreal Canadiens
1958-1959 Montreal Canadiens
1959-1960 Montreal Canadiens
1960-1961 Chicago Black Hawks
1961-1962 Toronto Maple Leafs
1962-1963 Toronto Maple Leafs
1963-1964 Toronto Maple Leafs
1964-1965 Montreal Canadiens
1965-1966 Montreal Canadiens
1966-1967 Toronto Maple Leafs
1967-1968 Montreal Canadiens
1968-1969 Montreal Canadiens
1969-1970 Boston Bruins
1970-1971 Montreal Canadiens
1971-1972 Boston Bruins
1972-1973 Montreal Canadiens
1973-1974 Philadelphia Flyers
1974-1975 Philadelphia Flyers
1975-1976 Montreal Canadiens
1976-1977 Montreal Canadiens
1977-1978 Montreal Canadiens
1978-1979 Montreal Canadiens
1979-1980 New York Islanders
1980-1981 New York Islanders
1981-1982 New York Islanders
1982-1983 New York Islanders
1983-1984 Edmonton Oilers
1984-1985 Edmonton Oilers
1985-1986 Montreal Canadiens
1986-1987 Edmonton Oilers
1987-1988 Edmonton Oilers
1989-1990 Edmonton Oilers
1990-1991 Pittsburgh Penguins
1991-1992 Pittsburgh Penguins
1992-1993 Montreal Canadiens
1993-1994 New Jersey Devils
1994-1995 New York Rangers
1995-1996 Colorado Avalanche
1996-1997 Detroit Red Wings
1997-1998 Detroit Red Wings
1998-1999 Dallas Stars