| | | | 0-0 (0-0) | Scrimmage | Bedford, MA | - | - |
| | | L 0-1 | 0-1 (0-1) | League | Holliston, MA | - | - |
| | | W 3-2 | 1-1 (1-1) | League | Holliston, MA | - | - |
| | | W 4-0 | 2-1 (2-1) | League | Holliston, MA | - | - |
| | | T 1-1 | 2-1-1 (2-1) | Non League | Holliston, MA | - | - |
| | | W 2-1 | 3-1-1 (3-1) | League | Medfield, MA | - | Watch |
| | | W 2-0 | 4-1-1 (4-1) | League | Westwood, MA | - | - |
| | | W 5-0 | 5-1-1 (5-1) | League | Medway, MA | - | - |
| | | W 9-0 | 6-1-1 (6-1) | League | Holliston, MA | - | - |
| | | W 3-1 | 7-1-1 (7-1) | League | Bellingham, MA | - | Watch |
| | | W 6-0 | 8-1-1 (8-1) | League | Holliston, MA | - | - |
| | | T 1-1 | 8-1-2 (8-1) | Non League | Dedham, MA | - | Watch |
| | | W 1-0 | 9-1-2 (9-1) | League | Holliston, MA | - | - |
| | | L 0-1 | 9-2-2 (9-2) | League | Hopkinton, MA | - | - |
| | | W 1-0 | 10-2-2 (10-2) | League | Ashland, MA | - | - |
| | | W 2-1 | 11-2-2 (10-2) | Non League | Wrentham, MA | - | - |
| | | W 4-0 | 12-2-2 (11-2) | League | Norwood, MA | - | - |
| | | L 1-4 | 12-3-2 (11-3) | League | Holliston, MA | - | - |
| | | W 3-1 | 13-3-2 (12-3) | League | Holliston, MA | - | - |
| | | | 13-3-2 (12-3) | Scrimmage | Needham, MA | - | - |