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The Toronto team known as the Maple Leafs won the Cup in the following seasons: 1931/32, 1941/42, 1944/45, 1946/47, 1947/48, 1948/49, 1950/51, 1962/63, 1963/64, and 1966/67. Also, before changing their name to the Maple Leafs, the Toronto St. Pats won in 1921/22 and an unnamed Toronto team (sometimes called the Arenas) won in 1918/19. As well, in the years preceding the formation of the NHL, a Toronto team called the Blueshirts won twice in 1914 when the Cup was a challenge trophy and a winning team could be challenged by another team at almost any time.
The Toronto Maple Leafs were in the Stanley Cup Finals 19 times
Winning it 11 times in:
1932, 1942, 1945, 1947, 1948, 1949, 1951, 1962, 1963, 1964 and 1967
and losing in the finals 8 times:
1933, 1935, 1936, 1938, 1939, 1940, 1959, 1960