| Year | Champion | Race Scores |
| 1923 | Wesleyan | Wesleyan 32, Amherst 44 (at Springfield); Wesleyan 24, Williams 31 |
| 1924 | Williams | at Williams 17, Wesleyan 40, Amherst 63 |
| 1925 | Wesleyan/Williams | at Wesleyan 33, Williams 33, Amherst 64 |
| 1926 | Wesleyan | Wesleyan 21, Williams 41, at Amherst 66 |
| 1927 | No title | at Wesleyan 21, Williams 38 |
| 1928 | No title | at Williams 19, Wesleyan 40 |
| 1929 | No title | (No race) |
| 1930 | Amherst | Amherst 36, Wesleyan 42, at Williams 48 |
| 1931 | Amherst | Amherst 24, at Wesleyan 37, Williams 71 |
| 1932 | Amherst | at Amherst 29, Wesleyan 42, Williams 52 |
| 1933 | Williams | at Williams 27, Amherst 39, Wesleyan 54 |
| 1934 | Amherst | Amherst 30, Williams 40, at Wesleyan 56 |
| 1935 | Williams | Williams 32, at Amherst 38, Wesleyan 51 |
| 1936 | Amherst | Amherst 26, at Wesleyan 42, Williams 57 |
| 1937 | Williams | at Williams 38, Wesleyan 39, Amherst 49 |
| 1938 | Amherst/Wesleyan | at Amherst 36, Wesleyan 36, Williams 48 |
| 1939 | Williams | Williams 33, at Wesleyan 34, Amherst 53 |
| 1940 | Wesleyan | Wesleyan 22, at Williams 33, Amherst 78 |
| 1941 | Williams | Williams 21, Wesleyan 42, at Amherst 68 |
| 1942 | Williams | Williams 32, at Wesleyan 43, Amherst 48 |
| 1943 | No title | (No race) |
| 1944 | No title | (No race) |
| 1945 | No title | (No race) |
| 1946 | Williams | at Williams 32, Amherst 35, Wesleyan 62 |
| 1947 | Williams | Williams 20, Wesleyan 51, at Amherst 65 |
| 1948 | Williams | Williams 34, Amherst 37, at Wesleyan 55 |
| 1949 | Williams | at Williams 26, Wesleyan 46, Amherst 55 |
| 1950 | Wesleyan | Wesleyan 27, Williams 31, at Amherst 62 |
| 1951 | Wesleyan | at Wesleyan 23, Williams 36, Amherst 70 |
| 1952 | Wesleyan | Wesleyan 17, at Williams 57, Amherst 64 |
| 1953 | Wesleyan | Wesleyan 29, Williams 38, at Amherst 53 |
| 1954 | Wesleyan | at Wesleyan 24, Amherst 31; Wesleyan 21, at Williams 36; Amherst def. Williams |
| 1955 | Amherst | at Amherst 26, Wesleyan 30; Williams 26, at Wesleyan 31; Amherst 22, at Williams 33 |
| 1956 | Wesleyan | at Wesleyan 24, Amherst 31; Wesleyan 22, at Williams 33; Amherst def. Williams |
| 1957 | Wesleyan | Wesleyan 23, at Amherst 32; at Wesleyan 22, Williams 36; Amherst def. Williams |
| 1958 | Wesleyan | at Wesleyan 20, Amherst 39; Wesleyan 23, at Williams 34; Williams def. Amherst |
| 1959 | Wesleyan | Wesleyan 20, at Amherst 38; at Wesleyan 16, Williams 43; Williams def. Amherst |
| 1960 | Wesleyan | at Wesleyan 19, Amherst 40; Wesleyan 18, at Williams 38; Williams def. Amherst |
| 1961 | Wesleyan | Wesleyan 18, at Amherst 45; at Wesleyan 22, Williams 35; Williams def. Amherst |
| 1962 | Wesleyan | at Wesleyan 16, Amherst 47; Wesleyan 19, at Williams 43; Williams def. Amherst |
| 1963 | Wesleyan | Wesleyan 15, at Amherst 49; at Wesleyan 15, Williams 50; Amherst def. Williams |
| 1964 | Wesleyan | at Wesleyan 15, Amherst 50; Wesleyan 19, at Williams 41; Amherst def. Williams |
| 1965 | Wesleyan | Wesleyan 18, at Amherst 45; at Wesleyan 19, Williams 42; Williams def. Amherst |
| 1966 | Wesleyan | at Wesleyan 24, Amherst 33; Wesleyan 20, at Williams 35; Amherst def. Williams |
| 1967 | Williams | at Amherst 25, Wesleyan 34; Williams 28, at Wesleyan 31; Williams def. Amherst |
| 1968 | Williams | at Wesleyan 26, Amherst 29; at Williams 25, Wesleyan 34; Williams def. Amherst |
| 1969 | Amherst | at Amherst 25, Wesleyan 32; at Wesleyan 22, Williams 34; Amherst def. Williams |
| 1970 | Williams | Amherst 27, at Wesleyan 30; at Williams 15, Wesleyan 49; Williams def. Amherst |
| 1971 | Williams | Williams 17, Amherst 40, at Wesleyan 77 |
| 1972 | Williams | Williams 17, at Amherst 40, Wesleyan 81 |
| 1973 | Williams | Williams 27, at Amherst 38, Wesleyan 65 |
| 1974 | Williams | Wesleyan 27, Amherst 28, Williams 18, Wesleyan 43; Williams def. Amherst |
| 1975 | No title* | Williams def. Amherst |
| 1976 | Williams | Williams 22, at Amherst 55, Wesleyan 59 |
| 1977 | Williams | Williams 25, Amherst 46, at Wesleyan 66 |
| 1978 | Williams | at Williams 26, Amherst 39, Wesleyan 64 |
| 1979 | Williams | Williams 22, at Amherst 37, Wesleyan 70 |
| 1980 | Williams | Williams 28, Amherst 44, at Wesleyan 52 |
| 1981 | Williams | at Williams 27, Amherst 41, Wesleyan 65 |
| 1982 | Williams | Williams 22, Wesleyan 43, at Amherst 66 |
| 1983 | Williams | Williams 28, at Wesleyan 30, Amherst 81 |
| 1984 | Wesleyan | at Wesleyan 30, Williams 36, Amherst 64 |
| 1985 | Williams | Williams 20, Wesleyan 55, at Amherst 58 |
| 1986 | Williams | Williams 32, Amherst 37, at Wesleyan 54 |
| 1987 | Amherst | Amherst 24, Wesleyan 38, at Williams 62 |
| 1988 | Williams | Williams 38, at Amherst 43, Wesleyan 44 |
| 1989 | Williams | Williams 20, at Wesleyan 48, Amherst 71 |
| 1990 | Williams | at Williams 20, Wesleyan 46, Amherst 69 |
| 1991 | Williams | Williams 17, Wesleyan 48, at Amherst 68 |
| 1992 | Williams | Williams 26, at Wesleyan 44, Amherst 62 |
| 1993 | Williams | at Williams 20, Wesleyan 41, Amherst 85 |
| 1994 | Williams | Williams 24, Wesleyan 35, at Amherst 72 |
| 1995 | Williams | Williams 15, Amherst 56, at Wesleyan 68 |
| 1996 | Williams | at Williams 20, Amherst 41, Wesleyan 75 |
| 1997 | Williams | Williams 22, at Amherst 46, Wesleyan 70 |
| 1998 | Williams | Williams 22, Amherst 42, at Wesleyan 73 |
| 1999 | Williams | at Williams 19, Amherst 48, Wesleyan 77 |
| 2000 | Williams | Williams 15, at Amherst 58, Wesleyan 62 |
| 2001 | Williams | Williams 15, Amherst 55, at Wesleyan 64 |
| 2002 | Williams | at Williams 22, Wesleyan 48, Amherst 60 |
| 2003 | Williams | Williams 34, at Amherst 36, Wesleyan 58 |
| 2004 | Williams | Williams 34, at Wesleyan 42, Amherst 47 |
| 2005 | Williams | at Williams 24, Wesleyan 34, Amherst 75 |
| 2006 | Williams | Williams 26, at Amherst 52, Wesleyan 55 |
| 2007 | Williams | Williams 24, Amherst 33, at Wesleyan 81 |
| 2008 | Williams | at Williams 21, Amherst 48, Wesleyan 71 |
| 2009 | Williams | Williams 25, at Amherst 35, Wesleyan 64 |
| 2010 | Williams | Williams 35, at Wesleyan 42, Amherst 54 |
| 2011 | Williams | at Williams 19, Wesleyan 57, Amherst 62 |
| 2012 | Williams | Williams 23, at Amherst 46, Wesleyan 61 |
| Summary of titles: Amherst - 8 (most recent: 1987) Wesleyan - 20 (most recent: 1984) Williams - 53 (most recent: 2012) Amherst/Wesleyan: 1 (1938) Wesleyan/Williams: 1 (1925) *Wesleyan did not participate in the Little Three race at Williams due to transporation difficulties. No champion was declared. |
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