| 2433 | Unscheduled | Milton High School Middle Field | Milton Celtic | - | Brookline Benfica | |
| 2436 | 9/19/20 4:30pm | Skyline Park | Brookline Benfica | 1 - 5 | Walpole Wildcats | |
| 2439 | 9/26/20 4:30pm | Skyline Park | Brookline Benfica | 1 - 5 | Medfield Warriors 8B | |
| 2442 | 10/3/20 1:00pm | Fessenden B/Kumin Loring | Newton B SOCA WARRIORS | 6 - 0 | Brookline Benfica | |
| 2445 | 10/10/20 4:30pm | Skyline Park | Brookline Benfica | 1 - 1 | Westwood Wolverines | |
| 2448 | 10/17/20 4:30pm | Skyline Park | Brookline Benfica | 1 - 4 | Milton Celtic | |
| 2449 | 10/24/20 3:00pm | Ellis 11v11 | Walpole Wildcats | 5 - 0 | Brookline Benfica | |
| 2454 | Unscheduled | Wheelock - 11v11-1 | Medfield Warriors 8B | - | Brookline Benfica | |
| 2457 | 11/7/20 10:30am | Beaver Country Day School | Brookline Benfica | 1 - 6 | Newton B SOCA WARRIORS | |
| 2458 | 11/14/20 5:00pm | Flahive Field HS Turf | Westwood Wolverines | 2 - 0 | Brookline Benfica | |
