| 1 | 6353 | 9/9/23 10:30am | Milton High School Middle Field | Milton Cardinals | 4 - 0 | Wellesley Wizards | |
| 2 | 6355 | 9/16/23 9:00am | BB&N Turf 1 - Grove Street | Watertown United | 0 - 4 | Milton Cardinals | |
| 3 | 6358 | 9/23/23 10:30am | Milton High School Middle Field | Milton Cardinals | 5 - 2 | Newton G Swifties | |
| 4 | 6361 | 9/30/23 11:30am | Madison Park- Upper (11v11) | South End Courage | 2 - 1 | Milton Cardinals | |
| 5 | 6363 | Unscheduled | Milton High School Middle Field | Milton Cardinals | F - 1 | Brookline Sevilla | Unable to reschedule after week 8 -- BK |
| 6 | 6368 | 10/14/23 9:00am | Sprague 3 (turf) | Wellesley Wizards | 0 - 2 | Milton Cardinals | |
| 7 | 6371 | 10/21/23 10:30am | Milton High School Middle Field | Milton Cardinals | 2 - 3 | Watertown United | |
| 8 | 6372 | 10/28/23 11:00am | Byrne (Carisbrooke) | Marlboro Panthers | 5 - 2 | Milton Cardinals | |
| 9 | 6375 | 11/4/23 10:30am | Milton High School Middle Field | Milton Cardinals | 1 - 3 | South End Courage | Score entered incorrectly BK |
| 10 | 6380 | 11/11/23 9:00am | Beaver Country Day School | Brookline Sevilla | 4 - 2 | Milton Cardinals | |
