| Team | Individual | ||||||
| Year | Site | Champion | Pts. | Runner-Up | Pts. | Champion | Time |
| 2022 | West. | Bridgewater | 42 | Westfield | 46 | Taban Manyok (Fi) | 26:14 |
| 2021 | Devens | Worcester | 49 | Fitchburg | 53 | Taban Manyok (Fi) | 26:08 |
| 2019 | Paxton | Bridgewater | 37 | Westfield | 60 | Trevor Wysong (B) | 25:56 |
| 2018 | Mt. Glock | Fitchburg | 46 | Bridgewater | 50 | Trevor Wysong (B) | 27:17 |
| 2017 | West. | Fitchburg | 30 | Bridgewater | 34 | Brian Amaral (F) | 25:41 |
| 2016 | Fitch. | Westfield | 34 | Fitchburg | 50 | Jake Hastings (F) | 26:02 |
| 2015 | Paxton | Fitchburg | 24 | Westfield | 41 | Mike Skelly (We) | 26:35 |
| 2014 | Mt. Glock | Westfield | 34 | Bridgewater | 51 | Andrew Sukeforth (B) | 26:30 |
| 2013 | So. Me. | Westfield | 18 | Fitchburg | 68 | Tim Shea (We) | 26:14 |
| 2012 | West. | Bridgewater | 27 | Westfield | 38 | Steven Wahome (B) | 25:36 |
| 2011 | Dart. | Westfield | 39 | Bridgewater | 45 | Alex Gomes (B) | 25:04 |
| 2010 | West. | Bridgewater | 45 | Westfield | 52 | Alex Gomes (B) | 25:36 |
| 2009 | West. | Westfield | 37 | Fitchburg | 48 | John Dacey (We) | 26:55 |
| 2008 | West. | Fitchburg | 53 | Bridgewater | 58 | Avery Bouchard (B) | 25:41 |
| 2007 | Wor. | Westfield | 46 | Worcester | 50 | Forest Wilbur (Wo) | 27:04 |
| 2006 | West. | Westfield | 29 | Mass Maritime | 62 | Andy Messer (We) | 26:32 |
| 2005 | Wor. | Mass Maritime | 39 | Bridgewater | 48 | Fabian Mejia (S) | 27:01 |
| 2004 | Fitch. | Westfield | 41 | Fitchburg | 66 | Fabain Mejia (S) | 24:13 |
| 2003 | West. | Fitchburg | 43 | Mass Maritime | 52 | Fabian Mejia (S) | 26:34 |
| 2002 | West. | Westfield | 30 | Bridgewater | 52 | Geoff Churchill (We) | 26:51 |
| 2001 | Fitch. | Bridgewater | 37 | West./Fitch. | 54 | Ryan Morin (B) | 24:59 |
| 2000 | West. | Bridgewater | 36 | Westfield | 53 | Daniel Smith (S) | 26:22 |
| 1999 | West. | Westfield | 21 | Bridgewater | 60 | Daniel Smith (S) | 26:48 |
| 1998 | Fitch. | Bridgewater | 37 | Westfield | 43 | Solomon Tsegai (B) | 24:27 |
| 1997 | Dart. | Bridgewater | 25 | Salem | 38 | Solomon Tsegai (B) | 25:11 |
| 1996 | West. | Westfield | 33 | Bridgewater | 48 | Solomon Tsegai (B) | 26:59 |
| 1995 | Fitch. | Westfield | 43 | Salem | 45 | James Pawlicki (S) | 24:34 |
| 1994 | Fram. | Salem | 36 | Westfield | 56 | John Bowser (S) | 26:35 |
| 1993 | West. | Westfield | 35 | Salem | 36 | David Gagnon (S) | 26:32 |
| 1992 | Fitch. | Westfield | 36 | Salem | 62 | James Gonsalves (We) | 24:21 |
| 1991 | Fram. | Westfield | 31 | Fitchburg | 32 | Jason Cullinane (F) | 26:25 |
| 1990 | West. | Westfield | 24 | Bridgewater | 60 | Mel Gonsalves (B) | 26:10 |
| 1989 | Fitch. | Westfield | 21 | Fitchburg | 65 | Chris Kiatos (We) | 24:07 |
| 1988 | Fram. | Westfield | 31 | Fitchburg | 68 | Steve Gaebel (We) | 27:07 |
| 1987 | West. | Westfield | 16 | Fitchburg | 60 | Ken Pliska (We) | 26:00 |
| 1986 | Fitch. | Westfield | 33 | Bridgewater | 52 | Greg Cornell (B) | 22:04 |
| 1985 | West. | Westfield | 36 | Fitchburg | 45 | Greg Cornell (B) | 24:01 |
| 1984 | N. Ad. | Westfield | 34 | Fitchburg | 56 | Scott Yakota (B) | 27:54 |
| 1983 | Bridge | Westfield | 30 | Fitchburg | 49 | Mike Churchill (F) | 26:08 |
| 1982 | West. | Fitchburg | 20 | Westfield | 44 | Brian Smith (F) | 25:20 |
| 1981 | Bost. | Westfield | 46 | Fitchburg | 48 | Dave Lavallee (S) | 25:12 |
| 1980 | Bost. | Fitchburg | 26 | Salem | 61 | Bob Thorne (B) | 25:24 |
| 1979 | Bost. | Boston State | 56 | Bridgewater | 64 | Steve Hunt (B) | 25:05 |
| 1978 | Bost. | Boston State | 25 | Westfield | 55 | Steve Hunt (B) | 24:34 |
| 1977 | Bost. | Boston State | 30 | Westfield | 41 | Jim Stronach (B) | 25:15 |
| 1976 | Bost. | Boston State | 31 | Westfield | 32 | John Goodwin (B) | 25:28 |
| 1975 | Bost. | Boston State | 19 | Westfield | 40 | Mark Duggan (B) | 25:43 |
| 1974 | Bost. | Boston State | Westfield | 43 | |||
| 1973 | Bost. | Boston State | 22 | Westfield | 40 | ||
| 1972 | Bost. | Westfield | 35 | Boston State | 48 | ||
| Team Championships: | |||||||
|
Westfield 25, Boston 7, Bridgewater 7, Fitchburg 7 , Salem 1 , Mass Maritime 1, Worcester 1 |
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