| 1 | 6352 | 9/9/23 9:00am | Beaver Country Day School | Brookline Sevilla | 0 - 0 | Watertown United | |
| 2 | 6355 | 9/16/23 9:00am | BB&N Turf 1 - Grove Street | Watertown United | 0 - 4 | Milton Cardinals | |
| 3 | 6359 | 9/23/23 12:00pm | Sprague 2 (turf) | Wellesley Wizards | 1 - 4 | Watertown United | |
| 4 | 6360 | 9/30/23 11:00am | Fessenden B / Kumin-Loring | Newton G Swifties | 2 - 3 | Watertown United | |
| 5 | 6364 | 10/7/23 9:00am | BB&N Turf 1 - Grove Street | Watertown United | 2 - 1 | South End Courage | |
| 6 | 6367 | 10/14/23 9:00am | Filippello Park - Grove St | Watertown United | 1 - 2 | Brookline Sevilla | |
| 7 | 6371 | 10/21/23 10:30am | Milton High School Middle Field | Milton Cardinals | 2 - 3 | Watertown United | |
| 8 | 6374 | 10/28/23 9:00am | Filippello Park - Grove St | Watertown United | 3 - 0 | Wellesley Wizards | |
| 9 | 6376 | 11/4/23 9:00am | Filippello Park - Grove St | Watertown United | 0 - 1 | Marlboro Panthers | |
| 10 | 6379 | 11/11/23 11:30am | Madison Park- Upper (11v11) | South End Courage | 1 - 2 | Watertown United | |
