| 1 | 6064 | 5/5/19 1:30pm | Pope John Paul II Park | Dorchester Cyclones | 3 - 0 | Brookline Boca | |
| 2 | 6067 | 4/13/19 1:30pm | Downes Field (oval) | Brookline Boca | 0 - 1 | Westwood Thunder | |
| 3 | 6072 | 4/20/19 11:45am | Pierce Middle School | Milton Independence | 8 - 1 | Brookline Boca | |
| 4 | 6074 | 4/27/19 1:30pm | Downes Field (oval) | Brookline Boca | 3 - 3 | Norwood Bolts | |
| 5 | 6077 | 5/4/19 11:45am | Esposito Realty Group Field - 1B | Mansfield Hornets II | 2 - 0 | Brookline Boca | |
| 6 | 6124 | 5/11/19 10:30am | Weeks A | Newton G Strikers | 2 - 3 | Brookline Boca | |
| 7 | 6127 | 5/18/19 11:45am | Teddy Ebersols Red Sox Field 9v9 (1) | Hill House United | 5 - 0 | Brookline Boca | |
| 8 | 6131 | 6/1/19 1:30pm | Downes Field (oval) | Brookline Boca | 0 - 4 | Natick Storm | |
| 9 | 6135 | 6/8/19 11:45am | Fessenden Field | D-S Cyclones | 7 - 0 | Brookline Boca | |
| 10 | 6138 | 6/15/19 1:30pm | Skyline Park | Brookline Boca | 3 - 2 | Canton Arsenal | |
