| | | | 0-0 (0-0) | Scrimmage | Northborough, MA | - | - |
| | | | 0-0 (0-0) | Scrimmage | Weston, MA | - | - |
| | | | 0-0 (0-0) | League | Bellingham, MA | - | Watch |
| | | L 1-3 | 0-1 (0-0) | Non League | Sutton, MA | - | Watch |
| | | T 1-1 | 0-1-1 (0-0-1) | League | Medway, MA | - | - |
| | | L 1-2 | 0-2-1 (0-1-1) | League | Medway, MA | - | - |
| | | L 1-3 | 0-3-1 (0-2-1) | League | Dedham, MA | - | Watch |
| | | W 1-0 | 1-3-1 (1-2-1) | League | Medway, MA | - | - |
| | | L 0-6 | 1-4-1 (1-3-1) | League | Holliston, MA | - | - |
| | | L 0-2 | 1-5-1 (1-4-1) | League | Medway, MA | - | - |
| | | W 2-0 | 2-5-1 (2-4-1) | League | Ashland, MA | - | - |
| | | W 2-0 | 3-5-1 (3-4-1) | League | Medway, MA | - | - |
| | | L 2-6 | 3-6-1 (3-5-1) | League | Medfield, MA | - | - |
| | | T 1-1 | 3-6-2 (3-5-2) | League | Medway, MA | - | - |
| | | W 2-1 | 4-6-2 (3-5-2) | Non League | Westborough, MA | - | - |
| | | | 4-6-2 (3-5-2) | League | Medway, MA | - | Watch |
| | | T 1-1 | 4-6-3 (3-5-3) | League | Millis, MA | - | - |
| | | W 2-0 | 5-6-3 (3-5-3) | Non League | Medway, MA | - | - |
| | | T 1-1 | 5-6-4 (3-5-4) | League | Norton, MA | - | Watch |
| | | W 3-0 | 6-6-4 (4-5-4) | League | Medway, MA | - | - |
| | | L 0-1 | 6-7-4 (4-5-4) | Non League | Bolton, MA | - | - |
| | | L 0-3 | 6-8-4 (4-6-4) | League | Dover, MA | - | - |
| | | W 2-0 | 7-8-4 (4-6-4) | Playoffs | Medway, MA | - | - |
| | | L 0-8 | 7-9-4 (4-6-4) | Playoffs | Medfield, MA | - | - |