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| 11 Grey Cup championship seasons: 1939, 1941, 1958, 1959, 1961, 1962, 1984, 1988, 1990, 2019, 2021 |
| Last Grey Cup championship: 2021, 4 seasons ago |
| Best finish: |
| beat Ott RghRiders for Grey Cup Championship in 1939 season |
| beat Ott RghRiders for Grey Cup Championship in 1941 season |
| beat Hamilton for Grey Cup Championship in 1958 season |
| beat Hamilton for Grey Cup Championship in 1959 season |
| beat Hamilton for Grey Cup Championship in 1961 season |
| beat Hamilton for Grey Cup Championship in 1962 season |
| beat Hamilton for Grey Cup Championship in 1984 season |
| beat British Columbia for Grey Cup Championship in 1988 season |
| beat Edmonton for Grey Cup Championship in 1990 season |
| beat Hamilton for Grey Cup Championship in 2019 season |
| beat Hamilton for Grey Cup Championship in 2021 season |
| TEAM | SEAS | RECORD | POINTS | DIV STAND | PLAYOFFS |
| Winnipeg | 1946 | 5-3 | 10 pts | 2nd WIFU | WCgy LTor |
| Winnipeg | 1947 | 5-3 | 10 pts | 1st WIFU | WCgy LTor |
| Winnipeg | 1948 | 3-9 | 6 pts | 3rd WIFU | missed playoffs |
| Winnipeg | 1949 | 2-12 | 4 pts | 4th WIFU | missed playoffs |
| Winnipeg | 1950 | 10-4 | 20 pts | 1st WIFU | bye WEdE LTor |
| Winnipeg | 1951 | 8-6 | 16 pts | 3rd WIFU | missed playoffs |
| Winnipeg | 1952 | 12-3-1 | 25 pts | 1st WIFU | bye LEdE |
| Winnipeg | 1953 | 8-8 | 16 pts | 3rd WIFU | WSsk WEdE LHam |
| Winnipeg | 1954 | 8-6-2 | 18 pts | 3rd WIFU | WSsk LEdE |
| Winnipeg | 1955 | 7-9 | 14 pts | 3rd WIFU | WSsk LEdE |
| Winnipeg | 1956 | 9-7 | 18 pts | 3rd WIFU | LSsk |
| Winnipeg | 1957 | 12-4 | 24 pts | 2nd WIFU | WCgy WEdE LHam |
| %Winnipeg | 1958 | 13-3 | 26 pts | 1st WIFU | bye WEdE WHam |
| %Winnipeg | 1959 | 12-4 | 24 pts | 1st WIFU | bye WEdE WHam |
| Winnipeg | 1960 | 14-2 | 28 pts | 1st WIFU | bye LEdE |
| %Winnipeg | 1961 | 13-3 | 26 pts | 1st West Cnf | bye WCgy WHam |
| %Winnipeg | 1962 | 11-5 | 22 pts | 1st West Cnf | bye WCgy WHam |
| Winnipeg | 1963 | 7-9 | 14 pts | 4th West Cnf | missed playoffs |
| Winnipeg | 1964 | 1-14-1 | 3 pts | 5th West Cnf | missed playoffs |
| Winnipeg | 1965 | 11-5 | 22 pts | 2nd West Cnf | WSsk WCgy LHam |
| Winnipeg | 1966 | 8-7-1 | 17 pts | 2nd West Cnf | WEdE LSsk |
| Winnipeg | 1967 | 4-12 | 8 pts | 4th West Cnf | missed playoffs |
| Winnipeg | 1968 | 3-13 | 6 pts | 5th West Cnf | missed playoffs |
| Winnipeg | 1969 | 3-12-1 | 7 pts | 5th West Cnf | missed playoffs |
| Winnipeg | 1970 | 2-14 | 4 pts | 5th West Cnf | missed playoffs |
| Winnipeg | 1971 | 7-8-1 | 15 pts | 3rd West Cnf | LSsk |
| Winnipeg | 1972 | 10-6 | 20 pts | 1st West Cnf | bye LSsk |
| Winnipeg | 1973 | 4-11-1 | 9 pts | 1st West Cnf | missed playoffs |
| Winnipeg | 1974 | 8-8 | 16 pts | 4th West Cnf | missed playoffs |
| Winnipeg | 1975 | 6-8-2 | 14 pts | 3rd West Cnf | LSsk |
| Winnipeg | 1976 | 10-6 | 20 pts | 2nd West Cnf | LEdE |
| Winnipeg | 1977 | 10-6 | 20 pts | 3rd West Cnf | LBC |
| Winnipeg | 1978 | 9-7 | 18 pts | 3rd West Cnf | LCgy |
| Winnipeg | 1979 | 4-12 | 8 pts | 4th West Cnf | missed playoffs |
| Winnipeg | 1980 | 10-6 | 20 pts | 2nd West Cnf | WCgy LEdE |
| Winnipeg | 1981 | 11-5 | 22 pts | 2nd West Cnf | LBC |
| Winnipeg | 1982 | 11-5 | 22 pts | 2nd West Div | WCgy LEdE |
| Winnipeg | 1983 | 9-7 | 18 pts | 2nd West Div | WEdE LBC |
| %Winnipeg | 1984 | 11-4-1 | 23 pts | 2nd West Div | WEdE WBC WHam |
| Winnipeg | 1985 | 12-4 | 24 pts | 2nd West Div | WEdE LBC |
| Winnipeg | 1986 | 11-7 | 22 pts | 3rd West Div | LBC |
| Winnipeg | 1987 | 12-6 | 24 pts | 1st East Div | bye LTor |
| %Winnipeg | 1988 | 9-9 | 18 pts | 2nd East Div | WHam WTor WBC |
| Winnipeg | 1989 | 7-11 | 14 pts | 3rd East Div | WTor LHam |
| %Winnipeg | 1990 | 12-6 | 24 pts | 1st East Div | bye WTor WEdE |
| Winnipeg | 1991 | 9-9 | 18 pts | 2nd East Div | WORR LTor |
| Winnipeg | 1992 | 11-7 | 22 pts | 1st East Div | bye WHam LCgy |
| Winnipeg | 1993 | 14-4 | 28 pts | 1st East Div | bye WHam LEdE |
| Winnipeg | 1994 | 13-5 | 26 pts | 1st East Div | WORR LBal |
| Winnipeg | 1995 | 7-11 | 14 pts | 5th Northern Div | missed playoffs |
| Winnipeg | 1996 | 9-9 | 18 pts | 3rd West Div | LEdE |
| Winnipeg | 1997 | 4-14 | 8 pts | 3rd East Div | missed playoffs |
| Winnipeg | 1998 | 3-15 | 6 pts | 4th East Div | missed playoffs |
| Winnipeg | 1999 | 6-12 | 12 pts | 4th East Div | missed playoffs |
| Winnipeg | 2000 | 7-10-1-1 | 16 pts | 3rd East Div | WHam LMtl |
| Winnipeg | 2001 | 14-4 | 28 pts | 1st East Div | bye WHam LCgy |
| Winnipeg | 2002 | 12-6 | 24 pts | 2nd West Div | WBC LEdE |
| Winnipeg | 2003 | 11-7 | 22 pts | 2nd West Div | LSsk |
| Winnipeg | 2004 | 7-11 | 14 pts | 4th West Div | missed playoffs |
| Winnipeg | 2005 | 5-13 | 10 pts | 5th West Div | missed playoffs |
| Winnipeg | 2006 | 9-9 | 18 pts | 3rd East Div | LTor |
| Winnipeg | 2007 | 10-7-1 | 21 pts | 2nd East Div | WMtl WTor LSsk |
| Winnipeg | 2008 | 8-10 | 16 pts | 2nd East Div | LEdE |
| Winnipeg | 2009 | 7-11 | 14 pts | 3rd East Div | missed playoffs |
| Winnipeg | 2010 | 4-14 | 8 pts | 4th East Div | missed playoffs |
| Winnipeg | 2011 | 10-8 | 20 pts | 1st East Div | bye WHam LBC |
| Winnipeg | 2012 | 6-12 | 12 pts | 3rd East Div | missed playoffs |
| Winnipeg | 2013 | 3-15 | 6 pts | 4th East Div | missed playoffs |
| Winnipeg | 2014 | 7-11 | 14 pts | 5th East Div | missed playoffs |
| Winnipeg | 2015 | 7-11 | 14 pts | 4th East Div | missed playoffs |
| Winnipeg | 2016 | 11-7 | 22 pts | 3rd West Div | LBC |
| Winnipeg | 2017 | 12-6 | 24 pts | 2nd West Div | LEdE |
| Winnipeg | 2018 | 10-8 | 20 pts | 3rd West Div | WSsk LCgy |
| %Winnipeg | 2019 | 11-7 | 22 pts | 3rd West Div | WCgy WSsk WHam |
| %Winnipeg | 2021 | 11-3 | 22 pts | 1st West Div | bye WSsk WHam |
| Winnipeg | 2022 | 15-3 | 30 pts | 1st West Div | bye WBC LTor |
| Winnipeg | 2023 | 14-4 | 28 pts | 1st West Div | bye WBC LMtl |
| Winnipeg | 2024 | 11-7 | 22 pts | 1st West Div | bye WSsk WTor |
| Winnipeg | 2025 | 10-8 | 20 pts | 4th West Div | LMtl |