| 1 | 4650 | 5/1/18 6:00pm | Millennium Park C | Parkway United White | 3 - 2 | Brookline Red Star | |
| 2 | 4623 | 4/14/18 1:30pm | Skyline Park | Brookline Red Star | 1 - 1 | South End Rush Splash | |
| 3 | 4626 | 5/17/18 6:30pm | Elm Bank 4 | Wellesley Wellesley FC | 2 - 1 | Brookline Red Star | |
| 4 | 4629 | 4/28/18 1:30pm | Skyline Park | Brookline Red Star | 5 - 0 | Milton Magic | |
| 5 | 4632 | 5/5/18 3:30pm | English High School 11v11 | JP Falcons | 2 - 0 | Brookline Red Star | |
| 6 | 4635 | 5/12/18 1:30pm | Skyline Park | Brookline Red Star | 0 - 1 | Parkway United White | |
| 7 | 4638 | 5/19/18 12:00pm | Madison Park- Upper (11v11) | South End Rush Splash | 3 - 0 | Brookline Red Star | |
| 8 | 4641 | 6/10/18 12:00pm | Cypress Field (High School) | Brookline Red Star | 5 - 2 | Canton Arsenal | |
| 9 | 4644 | 6/2/18 11:45am | Andrews Field | Milton Magic | F - 1 | Brookline Red Star | |
| 10 | 4647 | 6/9/18 3:00pm | Skyline Park | Brookline Red Star | 3 - 2 | JP Falcons | |
