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Years Montreal Won the Stanley CupThe answer depends on if you are asking about the Stanley Cup as we know it today and the team your asking about is the Montreal Canadians. Assuming it is, Montreal won it the following years: 1929-1931 (2 in a row) 1943-1946 (2 in a row) 1952-1953 1955-1960 (5 in a row) 1964-1966 (2 in a row) 1967-1969 (2 in a row) 1970-1971 1975-1979 (4 in a row) 1985-1986 1992-1993

If you wanted just "Montreal" in general, before 1915 the Stanley Cup was the Challenge Cup and Montreal won it 19 times.

Also, in 1915-1916, 1923-1924 & 1925-1926 the Montreal Canadians were PCHA & WCHL/WHL champions

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14y ago

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