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| 25 Stanley Cup championship seasons: 1918-19, 1923-24, 1924-25, 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, 1992-93 |
| Last Stanley Cup championship: 1992-93, 32 seasons ago |
| Best finish: |
| beat Ott Senators in Stanley Cup Finals in 1918-19 season |
| beat Ott Senators in Stanley Cup Finals in 1923-24 season |
| beat Ott Senators in Stanley Cup Finals in 1924-25 season |
| beat Boston in Stanley Cup Finals in 1929-30 season |
| beat Chicago in Stanley Cup Finals in 1930-31 season |
| beat Chicago in Stanley Cup Finals in 1943-44 season |
| beat Boston in Stanley Cup Finals in 1945-46 season |
| beat Boston in Stanley Cup Finals in 1952-53 season |
| beat Detroit in Stanley Cup Finals in 1955-56 season |
| beat Boston in Stanley Cup Finals in 1956-57 season |
| beat Boston in Stanley Cup Finals in 1957-58 season |
| beat Toronto in Stanley Cup Finals in 1958-59 season |
| beat Toronto in Stanley Cup Finals in 1959-60 season |
| beat Chicago in Stanley Cup Finals in 1964-65 season |
| beat Detroit in Stanley Cup Finals in 1965-66 season |
| beat St Louis in Stanley Cup Finals in 1967-68 season |
| beat St Louis in Stanley Cup Finals in 1968-69 season |
| beat Chicago in Stanley Cup Finals in 1970-71 season |
| beat Chicago in Stanley Cup Finals in 1972-73 season |
| beat Philadelphia in Stanley Cup Finals in 1975-76 season |
| beat Boston in Stanley Cup Finals in 1976-77 season |
| beat Boston in Stanley Cup Finals in 1977-78 season |
| beat NY Rangers in Stanley Cup Finals in 1978-79 season |
| beat Calgary in Stanley Cup Finals in 1985-86 season |
| beat Los Angeles in Stanley Cup Finals in 1992-93 season |
| TEAM | SEASON | RECORD | PTS | DIV STAND | CNF STAND | PLAYOFFS |
| Montreal | 1917-18 | 13-9-0 | 26 pts | T1st NHL | LTrA | |
| %Montreal | 1918-19 | 10-8-0 | 20 pts | 2nd NHL | WOtS | |
| Montreal | 1919-20 | 13-11-0 | 26 pts | 2nd NHL | missed playoffs | |
| Montreal | 1920-21 | 13-11-0 | 26 pts | 3rd NHL | missed playoffs | |
| Montreal | 1921-22 | 12-11-1 | 25 pts | 3rd NHL | missed playoffs | |
| Montreal | 1922-23 | 13- 9-2 | 28 pts | 2nd NHL | LOtS | |
| %Montreal | 1923-24 | 13-11-0 | 26 pts | 2nd NHL | WOtS | |
| %Montreal | 1924-25 | 17-11-2 | 36 pts | 3rd NHL | WTrS | |
| Montreal | 1925-26 | 11-24-1 | 23 pts | 7th NHL | missed playoffs | |
| Montreal | 1926-27 | 28-14-2 | 58 pts | 2nd Canadian | WMtM LOtS | |
| Montreal | 1927-28 | 26-11-7 | 59 pts | 1st Canadian | LMtM | |
| Montreal | 1928-29 | 22- 7-15 | 59 pts | 1st Canadian | LBos | |
| %Montreal | 1929-30 | 21-14-9 | 51 pts | 2nd Canadian | WChi WNYR WBos | |
| %Montreal | 1930-31 | 26-10-8 | 60 pts | 1st Canadian | WBos WChi | |
| Montreal | 1931-32 | 25-16-7 | 57 pts | 1st Canadian | LNYR | |
| Montreal | 1932-33 | 18-25-5 | 41 pts | 3rd Canadian | LNYR | |
| Montreal | 1933-34 | 22-20-6 | 50 pts | 2nd Canadian | LChi | |
| Montreal | 1934-35 | 19-23-6 | 44 pts | 3rd Canadian | LNYR | |
| Montreal | 1935-36 | 11-26-11 | 33 pts | 4th Canadian | missed playoffs | |
| Montreal | 1936-37 | 24-18-6 | 54 pts | 1st Canadian | WBos LDet | |
| Montreal | 1937-38 | 18-17-13 | 49 pts | 3rd Canadian | LChi | |
| Montreal | 1938-39 | 15-24-9 | 39 pts | 6th NHL | LDet | |
| Montreal | 1939-40 | 10-33-5 | 25 pts | 7th NHL | missed playoffs | |
| Montreal | 1940-41 | 16-26-6 | 38 pts | 6th NHL | LChi | |
| Montreal | 1941-42 | 18-27-3 | 39 pts | 6th NHL | LDet | |
| Montreal | 1942-43 | 19-19-12 | 50 pts | 4th NHL | LBos | |
| %Montreal | 1943-44 | 38- 5-7 | 83 pts | 1st NHL | WTor WChi | |
| Montreal | 1944-45 | 38- 8-4 | 80 pts | 1st NHL | LTor | |
| %Montreal | 1945-46 | 28-17-5 | 61 pts | 1st NHL | WChi WBos | |
| Montreal | 1946-47 | 34-16-10 | 78 pts | 1st NHL | WBos LTor | |
| Montreal | 1947-48 | 20-29-11 | 51 pts | 5th NHL | missed playoffs | |
| Montreal | 1948-49 | 28-23-9 | 65 pts | 3rd NHL | LDet | |
| Montreal | 1949-50 | 29-22-19 | 77 pts | 2nd NHL | LDet | |
| Montreal | 1950-51 | 25-30-15 | 65 pts | 3rd NHL | WDet LTor | |
| Montreal | 1951-52 | 34-26-10 | 78 pts | 2nd NHL | WBos LDet | |
| %Montreal | 1952-53 | 28-23-19 | 75 pts | 2nd NHL | WChi WBos | |
| Montreal | 1953-54 | 35-24-11 | 81 pts | 2nd NHL | WBos LDet | |
| Montreal | 1954-55 | 41-18-11 | 93 pts | 2nd NHL | WBos LDet | |
| %Montreal | 1955-56 | 45-15-10 | 100 pts | 1st NHL | WNYR WDet | |
| %Montreal | 1956-57 | 35-23-12 | 82 pts | 2nd NHL | WNYR WBos | |
| %Montreal | 1957-58 | 43-17-10 | 96 pts | 1st NHL | WDet WBos | |
| %Montreal | 1958-59 | 39-18-13 | 91 pts | 1st NHL | WChi WTor | |
| %Montreal | 1959-60 | 40-18-12 | 92 pts | 1st NHL | WChi WTor | |
| Montreal | 1960-61 | 41-19-10 | 92 pts | 1st NHL | LChi | |
| Montreal | 1961-62 | 42-14-14 | 98 pts | 1st NHL | LChi | |
| Montreal | 1962-63 | 28-19-23 | 79 pts | 3rd NHL | LTor | |
| Montreal | 1963-64 | 36-21-13 | 85 pts | 1st NHL | LTor | |
| %Montreal | 1964-65 | 36-23-11 | 83 pts | 2nd NHL | WTor WChi | |
| %Montreal | 1965-66 | 41-21-8 | 90 pts | 1st NHL | WTor WDet | |
| Montreal | 1966-67 | 32-25-13 | 77 pts | 2nd NHL | WNYR LTor | |
| %Montreal | 1967-68 | 42-22-10 | 94 pts | 1st East Div | WBos WChi WStL | |
| %Montreal | 1968-69 | 46-19-11 | 103 pts | 1st East Div | WNYR WBos WStL | |
| Montreal | 1969-70 | 38-22-16 | 92 pts | 5th East Div | missed playoffs | |
| %Montreal | 1970-71 | 42-23-13 | 97 pts | 3rd East Div | WBos WMin WChi | |
| Montreal | 1971-72 | 46-16-16 | 108 pts | 3rd East Div | LNYR | |
| %Montreal | 1972-73 | 52-10-16 | 120 pts | 1st East Div | WBuf WPhi WChi | |
| Montreal | 1973-74 | 45-24-9 | 99 pts | 2nd East Div | LNYR | |
| Montreal | 1974-75 | 47-14-19 | 113 pts | 1st Norris | 3rd NHL | bye WVan LBuf |
| %Montreal | 1975-76 | 58-11-11 | 127 pts | 1st Norris | 1st NHL | bye WChi WNYI WPhi |
| %Montreal | 1976-77 | 60- 8-12 | 132 pts | 1st Norris | 1st NHL | bye WStL WNYI WBos |
| %Montreal | 1977-78 | 59-10-11 | 129 pts | 1st Norris | 1st NHL | bye WDet WTor WBos |
| %Montreal | 1978-79 | 52-17-11 | 115 pts | 1st Norris | 2nd NHL | bye WTor WBos WNYR |
| Montreal | 1979-80 | 47-20-13 | 107 pts | 1st Norris | 3rd NHL | WHar LMin |
| Montreal | 1980-81 | 45-22-13 | 103 pts | 1st Norris | 3rd NHL | LEdm |
| Montreal | 1981-82 | 46-17-17 | 109 pts | 1st Adams | 2nd Wales | LQue |
| Montreal | 1982-83 | 42-24-14 | 98 pts | 2nd Adams | 3rd Wales | LBuf |
| Montreal | 1983-84 | 35-40-5 | 75 pts | 4th Adams | 8th Wales | WBos WQue LNYI |
| Montreal | 1984-85 | 41-27-12 | 94 pts | 1st Adams | 3rd Wales | WBos LQue |
| %Montreal | 1985-86 | 40-33-7 | 87 pts | 2nd Adams | 5th Wales | WBos WHar WNYR WCgy |
| Montreal | 1986-87 | 41-29-10 | 92 pts | 2nd Adams | 3rd Wales | WBos WQue LPhi |
| Montreal | 1987-88 | 45-22-13 | 103 pts | 1st Adams | 1st Wales | WHar LBos |
| Montreal | 1988-89 | 53-18-9 | 115 pts | 1st Adams | 1st Wales | WHar WBos WPhi LCgy |
| Montreal | 1989-90 | 41-28-11 | 93 pts | 3rd Adams | 3rd Wales | WBuf LBos |
| Montreal | 1990-91 | 39-30-11 | 89 pts | 2nd Adams | 2nd Wales | WBuf LBos |
| Montreal | 1991-92 | 41-28-11 | 93 pts | 1st Adams | 3rd Wales | WHar LBos |
| %Montreal | 1992-93 | 48-30-6 | 102 pts | 3rd Adams | 4th Wales | WQue WBuf WNYI WLA |
| Montreal | 1993-94 | 41-29-14 | 96 pts | 3rd Northeast | 5th East | LBos |
| Montreal | 1994-95 | 18-23-7 | 43 pts | 6th Northeast | --- East | missed playoffs |
| Montreal | 1995-96 | 40-32-10 | 90 pts | 3rd Northeast | 6th East | LNYR |
| Montreal | 1996-97 | 31-36-15 | 77 pts | 4th Northeast | 8th East | LNJ |
| Montreal | 1997-98 | 37-32-13 | 87 pts | 4th Northeast | 7th East | WPit LBuf |
| Montreal | 1998-99 | 32-39-11 | 75 pts | 5th Northeast | --- East | missed playoffs |
| Montreal | 1999-00 | 35-34-9-4 | 83 pts | 4th Northeast | --- East | missed playoffs |
| Montreal | 2000-01 | 28-40-8-6 | 70 pts | 5th Northeast | --- East | missed playoffs |
| Montreal | 2001-02 | 36-31-12-3 | 87 pts | 4th Northeast | 8th East | WBos LCar |
| Montreal | 2002-03 | 30-35-8-9 | 77 pts | 4th Northeast | --- East | missed playoffs |
| Montreal | 2003-04 | 41-30-7-4 | 93 pts | 3rd Northeast | 7th East | WBos LTB |
| Montreal | 2005-06 | 42-31-9 | 93 pts | 3rd Northeast | 7th East | LCar |
| Montreal | 2006-07 | 42-34-6 | 90 pts | 4th Northeast | --- East | missed playoffs |
| Montreal | 2007-08 | 47-25-10 | 104 pts | 1st Northeast | 1st East | WBos LPhi |
| Montreal | 2008-09 | 41-30-11 | 93 pts | 2nd Northeast | 8th East | LBos |
| Montreal | 2009-10 | 39-33-10 | 88 pts | 4th Northeast | 8th East | WWsh WPit LPhi |
| Montreal | 2010-11 | 44-30-8 | 96 pts | 2nd Northeast | 6th East | LBos |
| Montreal | 2011-12 | 31-35-16 | 78 pts | 5th Northeast | --- East | missed playoffs |
| Montreal | 2012-13 | 29-14-5 | 63 pts | 1st Northeast | 2nd East | LOtt |
| Montreal | 2013-14 | 46-28-8 | 100 pts | 3rd Atlantic | 5th East | WTB WBos LNYR |
| Montreal | 2014-15 | 50-22-10 | 110 pts | 1st Atlantic | 2nd East | WOtt LTB |
| Montreal | 2015-16 | 38-38-6 | 82 pts | 6th Atlantic | --- East | missed playoffs |
| Montreal | 2016-17 | 47-26-9 | 103 pts | 1st Atlantic | 2nd East | LNYR |
| Montreal | 2017-18 | 29-40-13 | 71 pts | 6th Atlantic | --- East | missed playoffs |
| Montreal | 2018-19 | 44-30-8 | 96 pts | 4th Atlantic | --- East | missed playoffs |
| Montreal | 2019-20 | 31-31-9 | 71 pts | 5th Atlantic | 12th East | WPit LPhi |
| Montreal | 2020-21 | 24-21-11 | 59 pts | 4th North Div | WTor WWpg WVGK LTB | |
| Montreal | 2021-22 | 22-49-11 | 55 pts | 8th Atlantic | --- East | missed playoffs |
| Montreal | 2022-23 | 31-45-6 | 68 pts | 8th Atlantic | --- East | missed playoffs |
| Montreal | 2023-24 | 30-36-16 | 76 pts | 8th Atlantic | --- East | missed playoffs |
| Montreal | 2024-25 | 40-31-11 | 91 pts | 5th Atlantic | T8th East | LWsh |