| | | W 3-0 | 1-0 (0-0) | Non League | Great Barrington, MA | - | Watch |
| | | W 3-0 | 2-0 (0-0) | Non League | Great Barrington, MA | - | Watch |
| | | | 2-0 (0-0) | Non League | Springfield, MA | - | - |
| | | W 3-0 | 3-0 (1-0) | League | Great Barrington, MA | - | - |
| | | L 1-3 | 3-1 (1-1) | League | Great Barrington, MA | - | Watch |
| | | | 3-1 (1-1) | Non League | Lee, MA | - | Watch |
| | | W 3-2 | 4-1 (1-1) | Non League | Chicopee, MA | - | - |
| | | W 3-1 | 5-1 (1-1) | Non League | Granby, MA | - | - |
| | | W 3-0 | 6-1 (1-1) | Non League | Great Barrington, MA | - | - |
| | | W 3-0 | 7-1 (2-1) | League | Sheffield, MA | - | Watch |
| | | L 0-3 | 7-2 (2-1) | Non League | Great Barrington, MA | - | Watch |
| | | L 1-3 | 7-3 (2-1) | Non League | Great Barrington, MA | - | - |
| | | | 7-3 (2-1) | Non League | Pittsfield, MA | - | - |
| | | | 7-3 (2-1) | Non League | Orange, MA | - | Watch |
| | | W 3-2 | 8-3 (3-1) | League | Great Barrington, MA | - | - |
| | | L 0-3 | 8-4 (3-2) | League | Mashpee, MA | - | - |