| 1 | 5371 | 4/8/23 9:00am | Filippello Park - Grove St | Watertown Woodchucks | 0 - 3 | Winchester Turbines | |
| 2 | 5376 | 6/2/23 6:00pm | Clarke Field | Lexington United Tigers | 0 - 0 | Watertown Woodchucks | Called for lightning, won’t be rescheduled |
| 3 | 5377 | 4/22/23 9:00am | HS Turf Field | Bedford Badgers | 0 - 2 | Watertown Woodchucks | |
| 4 | 5381 | 4/29/23 9:00am | Filippello Park - Grove St | Watertown Woodchucks | 3 - 1 | Winchester Flash | |
| 5 | 5384 | 5/6/23 10:30am | Grove St. (1A) | Belmont G8 Flyers | 2 - 2 | Watertown Woodchucks | |
| 6 | 5386 | 5/13/23 10:30am | Ryan Connolly Field 11v11 | Winchester Turbines | 2 - 1 | Watertown Woodchucks | |
| 7 | 5389 | 5/20/23 9:00am | Filippello Park - Grove St | Watertown Woodchucks | 0 - 2 | Lexington United Tigers | |
| 8 | 5393 | 5/27/23 9:00am | Filippello Park - Grove St | Watertown Woodchucks | 4 - 6 | Bedford Badgers | |
| 9 | 5395 | 6/4/23 9:00am | Skillings Grass 11v11 | Winchester Flash | 1 - 2 | Watertown Woodchucks | |
| 10 | 5399 | 6/10/23 6:00pm | Victory Turf | Watertown Woodchucks | 3 - 0 | Belmont G8 Flyers | |
