| 1 | 1293 | 4/6/19 12:00pm | Sprague 4B | Wellesley Breakaways | 1 - 1 | Brookline Chievo | |
| 2 | 1296 | 5/3/19 5:30pm | Adams | Lexington United Cheetahs | 4 - 0 | Brookline Chievo | |
| 3 | 1299 | 5/5/19 4:30pm | Healy Field #2 (DeFazio Field #4) | Needham Nitro | 3 - 1 | Brookline Chievo | |
| 4 | 1302 | 5/17/19 6:00pm | Weeks D | Newton G Wildcats | 3 - 1 | Brookline Chievo | |
| 5 | 1305 | 5/4/19 3:00pm | Coolidge Corner School | Brookline Chievo | 0 - 1 | Wayland Nutmeggers | |
| 6 | 1308 | 5/11/19 10:30am | Soule Recreation Center | Brookline Chievo | 3 - 1 | Wellesley Breakaways | |
| 7 | 1309 | 5/18/19 10:30am | Lincoln Fields1 | Lexington United Cheetahs | 0 - 1 | Brookline Chievo | |
| 8 | 1314 | 6/2/19 4:30pm | Healy Field #1 (DeFazio field #4) | Needham Nitro | 2 - 0 | Brookline Chievo | |
| 9 | 1317 | 6/8/19 10:30am | Soule Recreation Center | Brookline Chievo | 0 - 1 | Newton G Wildcats | |
| 10 | 1318 | 6/15/19 11:45am | Claypit Hill #5 | Wayland Nutmeggers | 7 - 0 | Brookline Chievo | |
