| 1 | 6601 | 9/7/19 1:30pm | Skyline Park | Brookline Benfica | 1 - 3 | Newton B Kings | |
| 2 | 6605 | 9/14/19 1:30pm | Skyline Park | Brookline Benfica | 1 - 0 | Westwood United | |
| 3 | 6610 | 9/21/19 1:45pm | Cutting | Sudbury Strikers | 3 - 2 | Brookline Benfica | |
| 4 | 6613 | 9/28/19 1:30pm | Beaver Country Day School | Brookline Los Rojos | 3 - 4 | Brookline Benfica | |
| 5 | 6617 | 10/5/19 1:30pm | Skyline Park | Brookline Benfica | 1 - 3 | Wellesley Raptors | |
| 6 | 6621 | 10/27/19 12:00pm | Wilson Field Bedford High School | Bedford Storm | 1 - 5 | Brookline Benfica | |
| 7 | 6625 | 10/19/19 2:30pm | Flahive Field HS Turf | Westwood United | 1 - 3 | Brookline Benfica | |
| 8 | 6629 | 10/26/19 1:30pm | Skyline Park | Brookline Benfica | 1 - 1 | Sudbury Strikers | |
| 9 | 6633 | 11/2/19 1:30pm | Skyline Park | Brookline Benfica | 6 - 0 | Belmont B8-3 Mustangs | |
| 10 | 6639 | 11/9/19 1:30pm | Fessenden A/Class of 1985 | Newton B Liverpool | 2 - 1 | Brookline Benfica | |
