Williams and Middlebury first met on the grid iron in 1906.
Williams leads the all-time series 68-27-1 through 2024.
| Year |
Winner |
Location
W/M |
Score |
| 2024 |
Middlebury |
M |
32-29, OT |
| 2023 |
Middlebury |
W |
12-10 |
| 2022 |
Middlebury |
M |
30-7 |
| 2021 |
Williams |
W |
41-13 |
| 2020 |
No contest due to pandemic |
|
|
| 2019 |
Middlebury |
M |
17-13 |
| 2018 |
Middlebury |
W |
21-10 |
| 2017 |
Williams |
M |
27-26 |
| 2016 |
Middlebury |
W |
49-23 |
| 2015 |
Middlebury |
M |
36-14 |
| 2014 |
Middlebury |
W |
23-20, OT |
| 2013 |
Middlebury |
M |
21-14 |
| 2012 |
Middlebury |
W |
30-13 |
| 2011 |
Williams |
M |
48-28 |
| 2010 |
Williams |
W |
41-17 |
| 2009 |
Williams |
M |
37-27 |
| 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 |
Williams |
W |
38-0 |
| 1906 |
Williams |
W |
16-0 |
