| | | W 4-3 | 1-0 (0-0) | Non League | South Deerfield, MA | - | - |
| | | W 2-1 | 2-0 (0-0) | Non League | Great Barrington, MA | - | - |
| | | | 2-0 (0-0) | Non League | Agawam, MA | - | - |
| | | | 2-0 (0-0) | Non League | Great Barrington, MA | - | - |
| | | L 1-4 | 2-1 (0-0) | Non League | Great Barrington, MA | - | - |
| | | | 2-1 (0-0) | Non League | Great Barrington, MA | - | - |
| | | PPD | 2-1 (0-0) | League | Great Barrington, MA | - | - |
| | | | 2-1 (0-0) | Non League | Pittsfield, MA | - | - |
| | | T 2-2 | 2-1-1 (0-0) | Non League | Westhampton, MA | - | - |
| | | W 1-0 | 3-1-1 (0-0) | Non League | Wilbraham, MA | - | - |
| | | | 3-1-1 (0-0) | League | Great Barrington, MA | - | - |
| | | L 0-3 | 3-2-1 (0-1) | League | Great Barrington, MA | - | - |
| | | | 3-2-1 (0-1) | Non League | Northampton, MA | - | Watch |
| | | | 3-2-1 (0-1) | League | Great Barrington, MA | - | - |
| | | | 3-2-1 (0-1) | Non League | Williamstown, MA | - | - |
| | | L 1-3 | 3-3-1 (0-1) | Non League | Great Barrington, MA | - | - |
| | | | 3-3-1 (0-1) | Non League | Amherst, MA | - | - |
| | | | 3-3-1 (0-1) | Non League | Williamstown, MA | - | - |
| | | CANC | 3-3-1 (0-1) | Non League | Great Barrington, MA | - | - |
| | | | 3-3-1 (0-1) | League | Great Barrington, MA | - | - |