| Team | Individual | ||||||
| Year | Site | Champion | Pts. | Runner-Up | Pts. | Champion | Time |
| 2022 | West. | Westfield | 31 | Fitchburg | 63 | Abby Murphy (F) | 19:16 |
| 2021 | Devens | Westfield | 37 | Bridgewater | 52 | Amy O'Sullivan (We) | 18:46 |
| 2019 | Paxton | Westfield | 34 | Bridgewater | 51 | Grace Phair (We) | 19:10 |
| 2018 | Mt. Greylock | Worcester | 38 | Westfield | 48 | Elisabeth Olson (Wo) | 20:03 |
| 2017 | West. | Worcester | 35 | Westfield | 41 | Jessie Cardin (We) | 18:19 |
| 2016 | Fitch. | Westfield | 24 | Worcester | 57 | Jessie Cardin (We) | 17:55 |
| 2015 | Paxton | Westfield | 38 | Bridgewater | 42 | Jessie Cardin (We) | 18:41 |
| 2014 | Mt. Greylock | Westfield | 28 | Bridgewater | 52 | Jessie Cardin (We) | 19:01 |
| 2013 | So. Me. | Westfield | 34 | Bridgewater | 44 | Krysta Zbikowski (B) | 19:29 |
| 2012 | West. | Westfield | 25 | Worcester | 55 | Molly Rouillard (B) | 18:00 |
| 2011 | Dart. | Westfield | 23 | Worcester | 51 | Molly Rouillard (B) | 18:37 |
| 2010 | West. | Westfield | 32 | Bridgewater | 41 | Molly Rouillard(B) | 19:05 |
| 2009 | West. | Westfield | 30 | Bridgewater | 44 | Kerry Arouca (We) | 19:10 |
| 2008 | West. | Westfield | 24 | Bridgewater | 72 | Kerry Arouca (We) | 18:44 |
| 2007 | Wor. | Westfield | 45 | Bridgewater | 60 | Nicole Mauro (B) | 19:43 |
| 2006 | West. | Westfield | 33 | Bridgewater | 63 | Alison Wesolowski (We) | 19:48 |
| 2005 | Wor. | Westfield | 20 | Bridgewater | 52 | Marianne Mealey (We) | 19:54 |
| 2004 | Fitch. | Westfield | 32 | Worcester | 43 | Olivia Patch (Wo) | 19:54 |
| 2003 | West. | Bridgewater | 38 | Westfield | 39 | Olivia Patch (Wo) | 18:53 |
| 2002 | West. | Bridgewater | 26 | Westfield | 29 | Kristen Iworski (B) | 19:28 |
| 2001 | Fitch. | Bridgewater | 28 | Westfield | 52 | Laura Karns (B) | 20:12 |
| 2000 | West. | Westfield | 53 | Bridgewater | 54 | Rhalda Jansen (F) | 20:18 |
| 1999 | West. | Westfield | 15 | Bridgewater | 77 | Diana Cares (We) | 19:04 |
| 1998 | Fitch. | Westfield | 23 | Fitchburg | 65 | Rhalda Jansen (F) | 20:54 |
| 1997 | Dart. | Westfield | 29 | Salem | 62 | Diana Cares (We) | 19:33 |
| 1996 | West. | Westfield | 26 | Fitchburg | 72 | Diana Cares (We) | 20:14 |
| 1995 | Fitch. | Fitchburg | 42 | Westfield | 63 | Kim Walsh (F) | 21:02 |
| 1994 | Fram. | Fitchburg | 27 | Framingham | 68 | K. Hennessy (B) | 19:35 |
| 1993 | West. | Fitchburg | 30 | Westfield | 53 | K. Hennessy (B) | 19:12 |
| 1992 | Fitch. | Westfield | 48 | Fitchburg | 49 | M. Lombard (F) | 19:45 |
| 1991 | Fram. | Westfield | 35 | Fitchburg | 44 | M. Lombard (F) | 20:00 |
| 1990 | West. | Salem | 39 | Westfield | 45 | Tina Anderson (S) | 19:46 |
| 1989 | Fitch. | Westfield | 52 | Salem | 62 | Michelle Penno (F) | 19:44 |
| 1988 | Fram. | Fitchburg | 37 | Westfield | 84 | K. Breswahan (F) | 20:09 |
| 1987 | West. | Fitchburg | 29 | North Adams | 80 | K. Breswahan (F) | 18:10 |
| 1986 | Fitch. | Fitchburg | 27 | Bridgewater | 48 | K. Breswahan (F) | 18:38 |
| 1985 | West. | Westfield | 25 | Fitchburg | 39 | Kathy Norton (We) | 18:19 |
| Team Championships: | |||||||
| Westfield 25, Fitchburg 6, Bridgewater 3, Worcester 2, Salem 1 | |||||||
The 2020 season was canceled due to the Covid-19 Pandemic
Updated 11/30/2022