| Fri | 09/05/08 | Jamboree | at Foxborough | |
| Week 1 | ||||
| Fri | 09/12/08 | Stoughton 12 | Longmeadow 24 | |
| King Philip 22 | Hopkinton 6 | |||
| Foxborough 0 | Bishop Feehan 14 | |||
| Franklin 6 | Attleboro 13 | |||
| Mansfield 7 | Dartmouth 9 | |||
| Oliver Ames vs | Holliston | Cancelled | ||
| Canton 8 | Quincy 7 | |||
| Sharon 0 | Silver Lake 27 | |||
| Week 2 | ||||
| Fri | 09/19/08 | King Philip 35 | Bellingham 0 | |
| Foxborough 7 | Dartmouth 14 | |||
| Stoughton 12 | Attleboro 26 | |||
| Franklin 18 | Milford 7 | |||
| Mansfield 22 | Marshfield 6 | |||
| Sat | 09/20/08 | Canton 12 | Madison Park 8 | |
| North Attleboro 9 | Bishop Feehan 13 | |||
| Oliver Ames 6 | Norton 35 | |||
| Sharon 0 | North Quincy 28 | |||
| Week 3 | ||||
| Sat | 09/27/08 | Oliver Ames 13 | Canton 25 | |
| Foxborough 7 | Central Catholic 28 | |||
| Sun | 09/28/08 | Sharon 12 | King Philip 46 | |
| North Attleboro 27 | Stoughton 0 | |||
| Mansfield 16 | Franklin 0 | |||
| Week 4 | ||||
| Fri | 10/03/08 | King Philip 20 | Oliver Ames 0 | |
| Mansfield 25 | Stoughton 12 | |||
| Sat | 10/04/08 | Sharon 6 | Weston 14 | |
| Foxborough 14 | North Attleboro 21 | |||
| Franklin 7 | Canton 0 | |||
| Week 5 | ||||
| Fri | 10/10/08 | Foxborough 7 | Franklin 24 | |
| Canton 7 | King Philip 28 | |||
| Stoughton 7 | Somerville 6 | |||
| Sat | 10/11/08 | Sharon 2 | Mansfield 0 | Game forfeited per MIAA rule |
| Oliver Ames 0 | North Attleboro 33 | |||
| Week 6 | ||||
| Fri | 10/17/08 | North Attleboro 21 | Franklin 7 | |
| Mansfield 0 | Oliver Ames 2 | Game forfeited per MIAA rule | ||
| King Philip 33 | Fairhaven 8 | |||
| Foxborough 0 | Stoughton 18 | |||
| Sat | 10/18/08 | Sharon 6 | Canton 21 | |
| Week 7 | ||||
| Fri | 10/24/08 | Canton 16 | Mansfield 34 | |
| Stoughton 34 | Oliver Ames 0 | |||
| King Philip 17 | North Attleboro 20 | |||
| Sharon 2 | Foxborough 48 | |||
| Franklin 42 | Taunton 14 | |||
| Week 8 | ||||
| Thurs | 10/30/08 | North Attleboro 48 | Sharon 21 | |
| Fri | 10/31/08 | Foxborough 42 | Oliver Ames 0 | |
| King Philip 7 | Mansfield 32 | |||
| Sat | 11/01/08 | Franklin 32 | Stoughton 14 | |
| Week 9 | ||||
| Fri | 11/07/08 | Franklin 35 | Sharon 8 | |
| Stoughton 12 | King Philip 16 | |||
| Canton 12 | Foxborough 38 | |||
| North Attleboro 7 | Mansfield 13 | |||
| Week 10 | ||||
| Fri | 11/14/08 | Stoughton 35 | Sharon 12 | |
| Franklin 32 | Oliver Ames 12 | |||
| North Attleboro 38 | Canton 0 | |||
| King Philip 56 | Foxborough 35 | |||
| Sat | 11/15/08 | Mansfield 30 | Norwich Free Academy 6 | |
| Week 11 | No Games | |||
| Week 12 | ||||
| Thu | 11/27/08 | North Attleboro 10 | Attleboro 12 | |
| Oliver Ames 20 | Sharon 19 | |||
| Mansfield 28 | Foxborough 0 | |||
| Stoughton 28 | Canton 2 | |||
| King Philip 22 | Franklin 12 | |||