The Montreal Canadiens have won the Stanley Cup 24 times, most recently in the 1992-93 season. They have won the Stanley cup more than any other team.
They won it in the 1914-15, 1923-24, 1929-30, 1930-31, 1943-44, 1945-46, 1952-53, 1955-56, 1956-57, 1957-58, 1958-59, 1959-60, 1964-65, 1965-66, 1967-68, 1968-69, 1970-71, 1972-73, 1975-76, 1976-77, 1977-78, 1978-79, 1985-86, and the 1992-93 seasons.
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The Montreal Canadiens have won the Stanley Cup 24times.
They won it in the 1914-15, 1923-24, 1929-30, 1930-31, 1943-44, 1945-46, 1952-53, 1955-56, 1956-57, 1957-58, 1958-59, 1959-60, 1964-65, 1965-66, 1967-68, 1968-69, 1970-71, 1972-73, 1975-76, 1976-77, 1977-78, 1978-79, 1985-86, and the 1992-93 seasons.
The Montreal Canadiens have won the Stanley Cup in the 1915-16, 1923-24, 1929-30, 1930-31, 1943-44, 1945-56, 1952-53, 1955-56, 1956-57, 1957-58, 1958-59, 1959-60, 1964-65, 1965-66, 1967-68, 1968-69, 1970-71, 1972-73, 1975-76, 1976-77, 1977-78, 1978-79, 1985-86 and the 1992-93 seasons, 24 times in total.
1916, 1924, 1930, 1931, 1944, 1946, 1953, 1956, 1957, 1958, 1959, 1960, 1965, 1966, 1968, 1969, 1971, 1973, 1976, 1977, 1978, 1979, 1986, 1993
1916, 1924, 1930, 1931, 1944, 1946, 1953, 1956, 1957, 1958, 1959, 1960, 1965, 1966, 1968, 1969, 1971, 1973, 1976, 1977, 1978, 1979, 1986, 1993
The Montreal Canadiens who have won the Stanley Cup 24 times!
The Toronto Maple Leafs have lost in the Stanley Cup Finals 8 times. Both the Montreal Canadiens and the Philadelphia Flyers have lost 6 times.
3 times: 1986, 1989 (win), and 2004. Additionally the 1924 Calgary Tigers of the WCHL lost while playing the Montreal Canadiens for the Stanley Cup.
The Montreal Canadiens won the Stanley Cup 5 times in the 1950s, in 53, 56, 57, 58, and 59,
The Montreal Canadiens won the Stanley Cup five times in a row in the 1960s. Runners up, like the Islanders, have won the Stanley cup four times in a row. Nowadays, it is almost impossible to win more than one in a row because of the salary cap.The Montreal Canadiens won five consecutive Stanley Cups between the 1955-56 and 1959-60 seasons.