| 2025 | Nov 22, 2025 | Vanderbilt 45, Kentucky 17 | FirstBank Stadium · Nashville, TN |
| 2024 | Oct 12, 2024 | Vanderbilt 20, Kentucky 13 | Kroger Field · Lexington, KY |
| 2023 | Sep 23, 2023 | Kentucky 45, Vanderbilt 28 | FirstBank Stadium · Nashville, TN |
| 2022 | Nov 12, 2022 | Vanderbilt 24, Kentucky 21 | Kroger Field · Lexington, KY |
| 2021 | Nov 13, 2021 | Kentucky 34, Vanderbilt 17 | FirstBank Stadium · Nashville, TN |
| 2020 | Nov 14, 2020 | Kentucky 38, Vanderbilt 35 | Kroger Field · Lexington, KY |
| 2019 | Nov 16, 2019 | Kentucky 38, Vanderbilt 14 | FirstBank Stadium · Nashville, TN |
| 2018 | Oct 20, 2018 | Kentucky 14, Vanderbilt 7 | Kroger Field · Lexington, KY |
| 2017 | Nov 11, 2017 | Kentucky 44, Vanderbilt 21 | FirstBank Stadium · Nashville, TN |
| 2016 | Oct 8, 2016 | Kentucky 20, Vanderbilt 13 | Kroger Field · Lexington, KY |
| 2015 | Nov 14, 2015 | Vanderbilt 21, Kentucky 17 | FirstBank Stadium · Nashville, TN |
| 2014 | Sep 27, 2014 | Kentucky 17, Vanderbilt 7 | Kroger Field · Lexington, KY |
| 2013 | Nov 16, 2013 | Vanderbilt 22, Kentucky 6 | FirstBank Stadium · Nashville, TN |
| 2012 | Nov 3, 2012 | Vanderbilt 40, Kentucky 0 | Kroger Field · Lexington, KY |
| 2011 | Nov 12, 2011 | Vanderbilt 38, Kentucky 8 | FirstBank Stadium · Nashville, TN |
| 2010 | Nov 13, 2010 | Kentucky 38, Vanderbilt 20 | Kroger Field · Lexington, KY |
| 2009 | Nov 14, 2009 | Kentucky 24, Vanderbilt 13 | FirstBank Stadium · Nashville, TN |
| 2008 | Nov 15, 2008 | Vanderbilt 31, Kentucky 24 | Kroger Field · Lexington, KY |
| 2007 | Nov 10, 2007 | Kentucky 27, Vanderbilt 20 | FirstBank Stadium · Nashville, TN |
| 2006 | Nov 11, 2006 | Kentucky 38, Vanderbilt 26 | Kroger Field · Lexington, KY |
| 2005 | Nov 12, 2005 | Kentucky 48, Vanderbilt 43 | FirstBank Stadium · Nashville, TN |
| 2004 | Nov 13, 2004 | Kentucky 14, Vanderbilt 13 | Kroger Field · Lexington, KY |
| 2003 | Nov 15, 2003 | Vanderbilt 28, Kentucky 17 | FirstBank Stadium · Nashville, TN |
| 2002 | Nov 16, 2002 | Kentucky 41, Vanderbilt 21 | Kroger Field · Lexington, KY |
| 2001 | Nov 10, 2001 | Kentucky 56, Vanderbilt 30 | FirstBank Stadium · Nashville, TN |
| 2000 | Nov 11, 2000 | Vanderbilt 24, Kentucky 20 | – |
| 1999 | Nov 13, 1999 | Kentucky 19, Vanderbilt 17 | – |
| 1998 | Nov 14, 1998 | Kentucky 55, Vanderbilt 17 | – |
| 1997 | Nov 15, 1997 | Kentucky 21, Vanderbilt 10 | – |
| 1996 | Nov 16, 1996 | Kentucky 25, Vanderbilt 0 | – |
| 1995 | Nov 4, 1995 | Vanderbilt 14, Kentucky 10 | – |
| 1994 | Nov 5, 1994 | Vanderbilt 24, Kentucky 6 | – |
| 1993 | Nov 6, 1993 | Vanderbilt 12, Kentucky 7 | – |
| 1992 | Nov 7, 1992 | Vanderbilt 20, Kentucky 7 | – |
| 1991 | Nov 9, 1991 | Vanderbilt 17, Kentucky 7 | – |
| 1990 | Nov 10, 1990 | Kentucky 28, Vanderbilt 21 | – |
| 1989 | Nov 11, 1989 | Kentucky 15, Vanderbilt 11 | – |
| 1988 | Nov 5, 1988 | Kentucky 14, Vanderbilt 13 | – |
| 1987 | Nov 7, 1987 | Vanderbilt 38, Kentucky 29 | – |
| 1986 | Nov 8, 1986 | Kentucky 34, Vanderbilt 22 | – |
| 1985 | Nov 9, 1985 | Vanderbilt 31, Kentucky 24 | – |
| 1984 | Nov 10, 1984 | Kentucky 27, Vanderbilt 18 | – |
| 1983 | Nov 5, 1983 | Kentucky 17, Vanderbilt 8 | – |
| 1982 | Nov 6, 1982 | Vanderbilt 23, Kentucky 10 | – |
| 1981 | Nov 7, 1981 | Kentucky 17, Vanderbilt 10 | – |
| 1980 | Nov 8, 1980 | Kentucky 31, Vanderbilt 10 | – |
| 1979 | Nov 10, 1979 | Kentucky 29, Vanderbilt 10 | – |
| 1978 | Nov 11, 1978 | Kentucky 53, Vanderbilt 2 | – |
| 1977 | Nov 5, 1977 | Kentucky 28, Vanderbilt 6 | – |
| 1976 | Nov 6, 1976 | Kentucky 14, Vanderbilt 0 | – |
| 1975 | Nov 8, 1975 | Vanderbilt 13, Kentucky 3 | – |
| 1974 | Nov 9, 1974 | Kentucky 38, Vanderbilt 12 | – |
| 1973 | Nov 10, 1973 | Kentucky 27, Vanderbilt 17 | – |
| 1972 | Nov 11, 1972 | Kentucky 14, Vanderbilt 13 | – |
| 1971 | Nov 6, 1971 | Kentucky 14, Vanderbilt 7 | – |
| 1970 | Nov 7, 1970 | Vanderbilt 18, Kentucky 17 | – |
| 1969 | Nov 8, 1969 | Vanderbilt 42, Kentucky 6 | – |
| 1968 | Nov 9, 1968 | Vanderbilt 6, Kentucky 0 | – |
| 1967 | Nov 11, 1967 | Kentucky 12, Vanderbilt 7 | – |
| 1966 | Nov 5, 1966 | Kentucky 14, Vanderbilt 10 | – |
| 1965 | Nov 6, 1965 | Kentucky 34, Vanderbilt 0 | – |
| 1964 | Nov 7, 1964 | Kentucky 22, Vanderbilt 21 | – |
| 1963 | Nov 9, 1963 | Kentucky 0, Vanderbilt 0 | – |
| 1962 | Nov 10, 1962 | Kentucky 7, Vanderbilt 0 | – |
| 1961 | Nov 11, 1961 | Kentucky 16, Vanderbilt 3 | – |
| 1960 | Nov 5, 1960 | Kentucky 27, Vanderbilt 0 | – |
| 1959 | Nov 7, 1959 | Vanderbilt 11, Kentucky 6 | – |
| 1958 | Nov 8, 1958 | Vanderbilt 0, Kentucky 0 | – |
| 1957 | Nov 9, 1957 | Vanderbilt 12, Kentucky 7 | – |
| 1956 | Nov 10, 1956 | Kentucky 7, Vanderbilt 6 | – |
| 1955 | Nov 5, 1955 | Vanderbilt 34, Kentucky 0 | – |
| 1954 | Nov 6, 1954 | Kentucky 19, Vanderbilt 7 | – |
| 1953 | Nov 7, 1953 | Kentucky 40, Vanderbilt 14 | – |
| 1948 | Oct 16, 1948 | Vanderbilt 26, Kentucky 7 | – |
| 1947 | Oct 18, 1947 | Kentucky 14, Vanderbilt 0 | – |
| 1946 | Oct 19, 1946 | Kentucky 10, Vanderbilt 7 | – |
| 1945 | Oct 20, 1945 | Vanderbilt 19, Kentucky 6 | – |
| 1942 | Oct 10, 1942 | Vanderbilt 7, Kentucky 6 | – |
| 1941 | Oct 11, 1941 | Vanderbilt 39, Kentucky 15 | – |
| 1940 | Oct 12, 1940 | Kentucky 7, Vanderbilt 7 | – |
| 1939 | Oct 7, 1939 | Kentucky 21, Vanderbilt 13 | – |
| 1938 | Oct 8, 1938 | Vanderbilt 14, Kentucky 7 | – |
| 1937 | Sep 25, 1937 | Vanderbilt 12, Kentucky 0 | – |
| 1928 | Nov 3, 1928 | Vanderbilt 14, Kentucky 7 | – |
| 1927 | Oct 29, 1927 | Vanderbilt 34, Kentucky 6 | – |
| 1922 | Nov 11, 1922 | Vanderbilt 9, Kentucky 0 | – |
| 1921 | Oct 15, 1921 | Vanderbilt 21, Kentucky 14 | – |
| 1920 | Oct 30, 1920 | Vanderbilt 20, Kentucky 0 | – |
| 1919 | Nov 1, 1919 | Vanderbilt 0, Kentucky 0 | – |
| 1918 | Nov 2, 1918 | Vanderbilt 33, Kentucky 0 | – |
| 1917 | Oct 20, 1917 | Vanderbilt 5, Kentucky 0 | – |
| 1916 | Oct 14, 1916 | Vanderbilt 45, Kentucky 0 | – |
| 1911 | Nov 11, 1911 | Vanderbilt 18, Kentucky 0 | – |
| 1907 | Oct 5, 1907 | Vanderbilt 40, Kentucky 0 | – |
| 1906 | Oct 6, 1906 | Vanderbilt 28, Kentucky 0 | – |