(Note: Only Wesleyan and Williams currently sponsor varsity programs. The most recent Little Three title was awarded in 2008.)
| Year | Champion | Race Order |
| 1977 | Williams | Williams, Wesleyan, Amherst |
| 1978 | Williams | Williams 6:11.2, Wesleyan 6:22.2, Amherst 6:52 |
| 1979 | Williams | Williams 7:14, Wesleyan 7:49.4, Amherst 7:56.4 |
| 1980 | Williams | Williams 7:00, Amherst 7:30, Wesleyan 7:35 |
| 1981 | Williams | Unknown |
| 1982 | Williams | Williams, Wesleyan, Amherst |
| 1983 | Williams | Williams, Wesleyan |
| 1984 | Williams | Williams 5:52.6, Wesleyan 5:52.9, Amherst 6:10 |
| 1985 | Williams | Williams, Wesleyan, Amherst |
| 1986 | Wesleyan | Wesleyan 7:24.6, Amherst 7:39.2, Williams 7:40.7 |
| 1987 | Wesleyan | Wesleyan 6:11, Amherst 6:18.6, Williams 6:22.4 |
| 1988 | Wesleyan | Wesleyan 6:55, Williams 6:56.4 |
| 1989 | Williams | Williams, Amherst |
| 1990 | Williams | Williams 7:16, Wesleyan 7:20.1, Amherst 7:34.23 |
| 1991 | Williams | Williams 7:29.6, Wesleyan 7:32.1, Amherst 8:35.1 |
| 1992 | Wesleyan | Wesleyan 7:54, Williams 8:15, Amherst 8:54.2 |
| 1993 | Williams | Williams 8:19.8, Wesleyan 8:21.4, Amherst |
| 1994 | Williams | Williams 6:05.2, Wesleyan 6:08.5 |
| 1995 | Williams | Williams 7:15.06, Wesleyan 7:20.54, Amherst 7:51.34 |
| 1996 | Wesleyan | Wesleyan 7:17.1, Williams 7:18.6, Amherst 8:05.9 |
| 1997 | Williams | Williams 7:44.37, Wesleyan 7:45.87 |
| 1998 | Williams | Williams 6:23.87, Wesleyan 6:31.3 |
| 1999 | Wesleyan | Wesleyan 6:48.57, Williams 6:49.32, Amherst 7:40.36 |
| 2000 | Williams | Williams 8:00.3, Wesleyan 8:02.4 |
| 2001 | Williams | Williams 6:52.7, Wesleyan 7:08.1, Amherst 7:27.9 |
| 2002 | Williams | Williams 7:29.0, Wesleyan 7:37.9, Amherst 7:48.3 |
| 2003 | Williams | Williams 7:13.9, Wesleyan 7:21.8 |
| 2004 | Williams | Williams 7:45.7, Wesleyan 8:01.9 |
| 2005 | Williams | Williams 7:06.9, Wesleyan 7:15.6 |
| 2006 | Williams | Williams 7:50.8, Wesleyan 8:27.6 |
| 2007 | Williams | Williams 6:56.6, Wesleyan 7:51.0 |
| 2008 | Williams | Williams 6:52.2, Wesleyan 7:14.1 |
| Summary of titles: Wesleyan - 6 (most recent: 1999) Williams - 26 (most recent: 2008) |
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