| | | | 0-0 (0-0) | Scrimmage | Gloucester, MA | - | - |
| | | | 0-0 (0-0) | Scrimmage | Gloucester, MA | - | - |
| | | | 0-0 (0-0) | Scrimmage | Manchester, MA | - | - |
| | | | 0-0 (0-0) | Scrimmage | Ipswich, MA | - | - |
| | | | 0-0 (0-0) | Scrimmage | Gloucester, MA | - | - |
| | | W 1-0 | 1-0 (1-0) | League | Gloucester, MA | - | Watch |
| | | L 2-5 | 1-1 (1-1) | League | Winthrop, MA | - | - |
| | | L 2-6 | 1-2 (1-1) | Non League | Boxford, MA | - | - |
| | | W 2-1 | 2-2 (2-1) | League | Gloucester, MA | - | Watch |
| | | W 1-0 | 3-2 (3-1) | League | Saugus, MA | - | - |
| | | L 0-1 | 3-3 (3-2) | League | Swampscott, MA | - | - |
| | | L 0-2 | 3-4 (3-3) | League | Gloucester, MA | - | Watch |
| | | W 3-0 | 4-4 (4-3) | League | Gloucester, MA | - | Watch |
| | | W 1-0 | 5-4 (4-3) | Non League | Gloucester, MA | - | Watch |
| | | T 2-2 | 5-4-1 (4-3) | Non League | Tewksbury, MA | - | - |
| | | | 5-4-1 (4-3) | Non League | Gloucester, MA | - | Watch |
| | | W 3-2 | 6-4-1 (5-3) | League | Gloucester, MA | - | Watch |
| | | L 1-2 | 6-5-1 (5-4) | League | Salem, MA | - | - |
| | | L 0-6 | 6-6-1 (5-4) | Non League | Malden, MA | - | - |
| | | W 2-0 | 7-6-1 (6-4) | League | Gloucester, MA | - | Watch |
| | | | 7-6-1 (6-4) | League | Danvers, MA | - | - |
| | | L 0-1 | 7-7-1 (6-4) | Non League | Rockport, MA | - | Watch |
| | | | 7-7-1 (6-4) | Scrimmage | Gloucester, MA | - | - |
| | | L 1-2 | 7-8-1 (6-5) | League | North Eastham, MA | - | - |