| | | | 0-0 (0-0) | Scrimmage | Hopkinton, MA | - | - |
| | | | 0-0 (0-0) | Scrimmage | North Dighton, MA | - | - |
| | | | 0-0 (0-0) | Non League | Upton, MA | - | Watch |
| | | | 0-0 (0-0) | Non League | Ashland, MA | - | - |
| | | | 0-0 (0-0) | Non League | Upton, MA | - | Watch |
| | | | 0-0 (0-0) | Non League | Medfield, MA | - | Watch |
| | | | 0-0 (0-0) | League | Upton, MA | - | Watch |
| | | L 1-2 | 0-1 (0-0) | Non League | Northborough, MA | - | - |
| | | | 0-1 (0-0) | Non League | Millbury, MA | - | - |
| | | | 0-1 (0-0) | League | Upton, MA | - | Watch |
| | | | 0-1 (0-0) | Non League | Upton, MA | - | Watch |
| | | | 0-1 (0-0) | Non League | Upton, MA | - | Watch |
| | | W 2-1 | 1-1 (1-0) | League | Whitinsville, MA | - | - |
| | | | 1-1 (1-0) | League | Upton, MA | - | Watch |
| | | | 1-1 (1-0) | League | Hopedale, MA | - | Watch |
| | | L 1-2 | 1-2 (1-1) | League | Upton, MA | - | Watch |
| | | | 1-2 (1-1) | Non League | Holden, MA | - | - |
| | | | 1-2 (1-1) | Non League | Upton, MA | - | Watch |
| | | | 1-2 (1-1) | Non League | Holliston, MA | - | - |
| | | | 1-2 (1-1) | Non League | Upton, MA | - | - |
| | | | 1-2 (1-1) | Non League | Bolton, MA | - | - |