| 1 | 5191 | 11/2/19 4:30pm | Beaver Country Day School | Brookline Ajax | 3 - 5 | Watertown WARRIORS | |
| 2 | 5196 | 9/14/19 9:00am | English High School 11v11 | JP Panthers | 1 - 7 | Brookline Ajax | |
| 3 | 5197 | 9/21/19 9:00am | Merchant Road Field 1 | Framingham FC Flyers | 0 - 7 | Brookline Ajax | |
| 4 | 5201 | 9/28/19 10:30am | Skyline Park | Brookline Ajax | 2 - 0 | Wellesley Chargers | |
| 5 | 5204 | 10/5/19 9:00am | Wilson Field Bedford High School | Bedford Banshees | 1 - 1 | Brookline Ajax | |
| 6 | 5206 | Unscheduled | Filippello Park - Grove St | Watertown WARRIORS | 1 - F | Brookline Ajax | |
| 7 | 5151 | 10/19/19 12:00pm | Beaver Country Day School | Brookline Ajax | 4 - 6 | D-S Arsenal | |
| 8 | 5152 | 10/26/19 9:00am | Lamson Field | Medway Mustangs | 2 - 5 | Brookline Ajax | |
| 9 | 5155 | 11/2/19 1:30pm | Beaver Country Day School | Brookline Ajax | 0 - 2 | Dedham Nor'Easter | |
| 10 | 5160 | 11/9/19 11:30am | AHS TURF | Attleboro Lightning | 0 - 2 | Brookline Ajax | |
