| 1969 | Tom Maynard | Colby | 9:27.0 - 2-mile |
| 1970 | |||
| 1971 | |||
| 1972 | |||
| 1973 | Bill Wilson | Bowdoin | 9:23.0 - 2-mile |
| 1974 | |||
| 1975 | Bruce Merrill | Bates | 9:14.7 - 2-mile |
| Paul Oparowski | Bates | 9:14.7 - 2-mile | |
| 1976 | |||
| 1977 | |||
| 1978 | Paul Oparowski | Bates | 9:06.3 - 2-mile |
| 1979 | |||
| 1980 | Kim Wettlaufer | Bates | 9:02.3 - 2-mile |
| 1981 | Todd Coffin | Colby | 8:30.2 - 3k |
| 1982 | Todd Coffin | Colby | 9:05.2 - 2-mile |
| 1983 | Todd Coffin | Colby | 8:17.6 - 3k |
| 1984 | Jerry Clapper | Maine | 8:54.3 - 2-mile |
| 1985 | Art Feeley | Colby | 8:38.3 - 3k |
| 1986 | John Fitzgerald | Bates | 9:04 - 2-mile |
| 1987 | James Huleatt | Bates | 9:13.0 - 2-mile |
| 1988 | Bill Derry | Colby | 15:06.68 |
| 1989 | Pat O’Malley | Maine | 15:17.07 |
| 1990 | Bob Sprague | Bates | 16:07.00 |
| 1991 | Joseph Sears | Bates | 15:19.41 |
| 1992 | Bill Callahan | Bowdoin | 15:21.22 |
| 1993 | Craig Sarney | Bates | 15:31.08 |
| Aldrich | Bates | 15:31.08 | |
| 1994 | James Johnson | Bowdoin | 16:00.83 |
| 1995 | Bill Callahan | Bowdoin | 16:09.11 |
| 1996 | no meet held | ||
| 1997 | James Johnson | Bowdoin | 15:11.07 |
| 1998 | Mike Danahy | Bates | 15:11.0 |
| 1999 | Mike Danahy | Bates | 15:05.7 |
| 2000 | Patrick Vardaro | Bowdoin | 15:27.36 |
| 2001 | Patrick Vardaro | Bowdoin | 15:22.67 |
| 2002 | Patrick Vardaro | Bowdoin | 14:53.85 |
| 2003 | Patrick Vardaro | Bowdoin | 15:03.86 |