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Montreal Canadiens Stanley Cup Winning Teams Cup Year Opponent Games Conn Smythe Stanley Cup 1. 1915-16 Portland 3-2 -- 2. 1923-24 Calgary 2-0 -- 3. 1929-30 Boston 2-0 -- 4. 1930-31 Chicago 3-2 -- 5. 1943-44 Chicago 4-0 -- 6. 1945-46 Boston 4-1 -- 7. 1952-53 Boston 4-1 -- 8. 1955-56 Detroit 4-1 -- 9. 1956-57 Boston 4-1 -- 10. 1957-58 Boston 4-2 -- 11. 1958-59 Toronto 4-1 -- 12. 1959-60 Toronto 4-0 -- 13. 1964-65 Chicago 4-3 Jean Beliveau 14. 1965-66 Detroit 4-2 -- 15. 1967-68 St. Louis 4-0 -- 16. 1968-69 St. Louis 4-0 Serge Savard 17. 1970-71 Chicago 4-3 Ken Dryden 18. 1972-73 Chicago 4-2 Yvan Cournoyer 19. 1975-76 Philadelphia 4-0 -- 20. 1976-77 Boston 4-0 Guy Lafleur 21. 1977-78 Boston 4-2 Larry Robinson 22. 1978-79 NY Rangers 4-1 Bob Gainey 23. 1985-86 Calgary 4-1 Patrick Roy 24. 1992-93 Los Angeles 4-1 Patrick Roy