Vs. Middlebury
Williams and Middlebury first met on the grid iron in 1906.
Williams leads the all-time series 63-17-1 throgh 2008.
| Year | Winner | Location W/M | Score |
| 2008 | Williams | W | 50-45 |
| 2007 | Williams | M | 30-22 |
| 2006 | Williams | W | 40-9 |
| 2005 | Williams | M | 39-18 |
| 2004 | Williams | W | 17-16 |
| 2003 | Williams | M | 35-25 |
| 2002 | Williams | W | 27-24 |
| 2001 | Williams | M | 23-3 |
| 2000 | Middlebury | W | 7-0 |
| 1999 | Williams | M | 25-0 |
| 1998 | Williams | W | 38-14 |
| 1997 | Williams | M | 25-20 |
| 1996 | Williams | W | 16-0 |
| 1995 | Williams | M | 35-3 |
| 1994 | Williams | W | 40-0 |
| 1993 | Williams | M | 14-6 |
| 1992 | Middlebury | W | 3-0 |
| 1991 | Williams | M | 26-14 |
| 1990 | Williams | W | 17-6 |
| 1989 | Williams | M | 22-0 |
| 1988 | Williams | W | 21-0 |
| 1987 | Middlebury | W | 17-7 |
| 1986 | Williams | M | 17-7 |
| 1985 | Williams | W | 7-6 |
| 1984 | Williams | M | 17-14 |
| 1983 | Williams | W | 29-14 |
| 1982 | Middlebury | M | 24-23 |
| 1981 | Williams | W | 27-7 |
| 1980 | Tie | M | 14-14 |
| 1979 | Middlebury | W | 10-9 |
| 1978 | Williams | M | 33-12 |
| 1977 | Middlebury | W | 27-0 |
| 1976 | Middlebury | M | 3-0 |
| 1975 | Williams | M | 22-0 |
| 1974 | Middlebury | W | 25-10 |
| 1973 | Middlebury | M | 35-21 |
| 1972 | Middlebury | W | 23-13 |
| 1971 | Williams | M | 33-28 |
| 1970 | Williams | W | 31-14 |
| 1969 | Williams | M | 37-14 |
| 1968 | Williams | W | 48-14 |
| 1967 | Williams | M | 20-0 |
| 1966 | Williams | W | 20-0 |
| 1965 | Williams | M | 28-12 |
| 1964 | Williams | W | 23-0 |
| 1963 | Williams | M | 16-8 |
| 1962 | Williams | W | 10-0 |
| 1961 | Williams | M | 12-0 |
| 1960 | Middlebury | W | 16-0 |
| 1959 | Williams | M | 26-8 |
| 1958 | Williams | W | 31-0 |
| 1957 | Williams | M | 32-19 |
| 1956 | Williams | W | 33-7 |
| 1955 | Williams | M | 26-0 |
| 1954 | Middlebury | W | 19-13 |
| 1953 | Williams | M | 7-0 |
| 1952 | Williams | W | 9-0 |
| 1947 | Middlebury | W | 19-7 |
| 1946 | Williams | W | 12-6 |
| 1942 | Williams | W | 41-0 |
| 1941 | Williams | W | 33-0 |
| 1940 | Williams | W | 14-6 |
| 1939 | Middlebury | W | 7-0 |
| 1938 | Williams | W | 13-0 |
| 1937 | Williams | W | 7-0 |
| 1935 | Williams | M | 40-0 |
| 1934 | Williams | W | 27-19 |
| 1933 | Middlebury | W | 3-0 |
| 1932 | Middlebury | M | 18-7 |
| 1930 | Williams | W | 26-0 |
| 1929 | Williams | M | 13-0 |
| 1928 | Williams | W | 20-0 |
| 1927 | Williams | W | 20-13 |
| 1926 | Williams | W | 32-0 |
| 1922 | Williams | M | 14-7 |
| 1921 | Middlebury | W | 7-3 |
| 1919 | Williams | W | 19-0 |
| 1917 | Williams | W | 39-7 |
| 1908 | Williams | W | 56-0 |
| 1907 | Willaims | W | 38-0 |
| 1906 | Willaims | W | 16-0 |
