(Note: Only Wesleyan and Williams currently sponsor varsity programs. The most recent Little Three title was awarded in 2008, the last year Amherst had a well-founded club program.)
| Year | Champion | Race Order |
| 1968 | Wesleyan | Wesleyan 6:13.5, Amherst 6:20.1; Wesleyan 5:12, Williams 5:49 |
| 1969 | Wesleyan | Wesleyan 6:58, Amherst 7:07, Williams 7:14 |
| 1970 | Wesleyan | Wesleyan 6:54, Amherst 7:14, Williams 7:20 |
| 1971 | Wesleyan | Wesleyan 6:03.8, Amherst 6:16, Williams 6:24 |
| 1972 | Amherst | Amherst 6:11.5, Wesleyan 6:15, Williams 6:22 |
| 1973 | Wesleyan | Wesleyan, Amherst, Williams |
| 1974 | Wesleyan | Wesleyan, Amherst |
| 1975 | Amherst | Amherst 5:06, Wesleyan 5:13, Williams 5:23 |
| 1976 | Wesleyan | Wesleyan 6:13.0, Williams 6:13.5, Amherst 6:20 |
| 1977 | Wesleyan | Wesleyan 6:06, Williams 6:09, Amherst 6:21 |
| 1978 | Williams | Williams, Wesleyan, Amherst |
| 1979 | Wesleyan | Wesleyan 6:33, Amherst 6:35.9, Williams 6:40.5 |
| 1980 | Williams | Williams 6:23.5, Wesleyan 6:26.2, Amherst 6:31.2 |
| 1981 | Williams | Williams, Wesleyan, Amherst |
| 1982 | Amherst | Amherst, Wesleyan, Williams |
| 1983 | Amherst | Amherst, Williams, Wesleyan |
| 1984 | Wesleyan | Wesleyan, Williams, Amherst |
| 1985 | Williams | Williams, Wesleyan |
| 1986 | Wesleyan | Wesleyan 6:35.23, Williams 6:43.41 |
| 1987 | Wesleyan | Wesleyan 5:27.6, Williams 5:42.6, Amherst 5:57.0 |
| 1988 | Williams | Williams 5:43, Wesleyan 5:50, Amherst 6:13 |
| 1989 | Williams | Williams 6:41.1, Wesleyan 6:42.8, Amherst |
| 1990 | Williams | Williams 6:08, Wesleyan 6:13.2, Amherst 6:40.2 |
| 1991 | Wesleyan | Wesleyan 6:21.6, Williams 6:22.3, Amherst 6:58.2 |
| 1992 | Williams | Williams 6:40.3, Wesleyan 6:54.3, Amherst 6:57.3 |
| 1993 | Wesleyan | Wesleyan 7:20.3, Williams 7:28.3, Amherst 7:34.8 |
| 1994 | Williams | Williams 6:05.2, Wesleyan 6:08.5, Amherst 6:40.5 |
| 1995 | Williams | Williams 6:52.1, Wesleyan 7:09.2 |
| 1996 | Williams | Williams 6:14.3, Wesleyan 6:30.3 |
| 1997 | Williams | Williams 6:43.5, Wesleyan 6:57.5 |
| 1998 | Williams | Williams 5:51.2, Wesleyan 5:52.1 |
| 1999 | Wesleyan | Wesleyan 5:49.1, Williams 5:52.1, Amherst 6:10.1 |
| 2000 | Williams | Williams 7:06.5, Wesleyan 7:07.5, Amherst 7:42.9 |
| 2001 | Williams | Williams 6:17.9, Wesleyan 6:18.8, Amherst 6:36.0 |
| 2002 | Williams | Williams 6:23.6, Wesleyan 6:28.2 |
| 2003 | Williams | Williams 6:21.4, Wesleyan 6:28.3, Amherst 6:38.2 |
| 2004 | Williams | Williams 6:34.4, Wesleyan 6:38.5 |
| 2005 | Williams | Williams 6:18.4, Wesleyan 6:20.9, Amherst 6:43.6 |
| 2006 | Williams | Williams 6:30.7, Wesleyan 6:32.3 |
| 2007 | Wesleyan | Wesleyan 6:04.5, Williams 6:08.1 |
| 2008 | Williams | Williams 6:07.9, Wesleyan 6:12.9 |
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NOTE - to see results between Wesleyan and Williams from 2009 to the present, see the complete Wesleyan-Williams results page by clicking < here > Summary of titles: |
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