| 1 | 5492 | 9/7/19 12:30pm | Peirce Field (HS turf) | Arlington Avalanche | 6 - 0 | Brookline Arsenal | |
| 2 | 5495 | 9/14/19 10:30am | Beaver Country Day School | Brookline Arsenal | 1 - 1 | Winchester Reds | |
| 3 | 5499 | 9/21/19 2:00pm | Clarke Field | Lexington Jaguars | 5 - 1 | Brookline Arsenal | |
| 4 | 5500 | 9/28/19 10:30am | PQ (1A) | Belmont G8-3 Heat | 4 - 0 | Brookline Arsenal | |
| 5 | 5504 | 10/5/19 12:00pm | Beaver Country Day School | Brookline Arsenal | 0 - 4 | Wellesley Storm | |
| 6 | 5507 | 10/12/19 12:00pm | Beaver Country Day School | Brookline Arsenal | 0 - 3 | Arlington Avalanche | |
| 7 | 5511 | 10/19/19 10:30am | McDonald Field 11v11 | Winchester Reds | 6 - 1 | Brookline Arsenal | |
| 8 | 5514 | 10/26/19 10:30am | Beaver Country Day School | Brookline Arsenal | 1 - 1 | Lexington Jaguars | |
| 9 | 5516 | 11/2/19 10:30am | Beaver Country Day School | Brookline Arsenal | 1 - 4 | Belmont G8-3 Heat | |
| 10 | 5519 | 11/9/19 9:00am | Elm Bank 4 | Wellesley Storm | 2 - 0 | Brookline Arsenal | |
