| | | | 0-0 (0-0) | Scrimmage | Ashland, MA | - | - |
| | | | 0-0 (0-0) | Scrimmage | Natick, MA | - | - |
| | | | 0-0 (0-0) | Non League | Medfield, MA | - | Watch |
| | | | 0-0 (0-0) | League | Ashland, MA | - | - |
| | | | 0-0 (0-0) | League | Hopkinton, MA | - | - |
| | | | 0-0 (0-0) | League | Ashland, MA | - | - |
| | | | 0-0 (0-0) | League | Ashland, MA | - | - |
| | | | 0-0 (0-0) | League | Ashland, MA | - | - |
| | | L 0-1 | 0-1 (0-1) | League | Medway, MA | - | - |
| | | | 0-1 (0-1) | Non League | Ashland, MA | - | - |
| | | W 6-0 | 1-1 (1-1) | League | Bellingham, MA | - | Watch |
| | | | 1-1 (1-1) | Non League | Wayland, MA | - | - |
| | | | 1-1 (1-1) | Non League | Dedham, MA | - | - |
| | | | 1-1 (1-1) | Non League | Ashland, MA | - | - |
| | | | 1-1 (1-1) | League | Holliston, MA | - | - |
| | | | 1-1 (1-1) | League | Ashland, MA | - | - |
| | | | 1-1 (1-1) | League | Ashland, MA | - | - |
| | | | 1-1 (1-1) | League | Westwood, MA | - | Watch |
| | | | 1-1 (1-1) | League | Norwood, MA | - | - |
| | | | 1-1 (1-1) | Non League | Ashland, MA | - | - |