| 1 | 1052 | 9/7/19 4:30pm | Soule Recreation Center | Brookline Rangers | 1 - 8 | Hopkinton B4 Academy Orange | |
| 2 | 1054 | 9/14/19 1:30pm | Lincoln Fields1 | Lexington Falcons | 3 - 0 | Brookline Rangers | |
| 3 | 1057 | 9/21/19 4:30pm | Soule Recreation Center | Brookline Rangers | 3 - 4 | C-C Tornados | |
| 4 | 1062 | 9/28/19 3:00pm | Coolidge Corner School | Brookline Rangers | 1 - 0 | Belmont B4-2 Cougars | |
| 5 | 1063 | 10/5/19 1:00pm | Flerra B | A-B Phoenix | 3 - 1 | Brookline Rangers | |
| 6 | 1067 | Unscheduled | Cornell's Field | Hopkinton B4 Academy Orange | - | Brookline Rangers | |
| 7 | 1070 | 10/19/19 4:30pm | Soule Recreation Center | Brookline Rangers | 1 - 5 | Lexington Falcons | |
| 8 | 1073 | 10/26/19 1:00pm | Banta Davis 7 Front | C-C Tornados | 2 - 0 | Brookline Rangers | |
| 9 | 1077 | 11/2/19 1:00pm | PQ (1C) | Belmont B4-2 Cougars | 6 - 2 | Brookline Rangers | |
| 10 | 1080 | 11/9/19 3:00pm | Beaver Country Day School | Brookline Rangers | 2 - 6 | Belmont B4-3 Jaguars | |
