| 1 | 5657 | 9/6/25 2:30pm | BB&N Turf 1 - Grove Street | Watertown Warriors | 0 - 0 | Brookline Man City | |
| 2 | 5660 | 9/13/25 1:30pm | Beaver Country Day School | Brookline Man City | - | Lexington Minutemen | |
| 3 | 5664 | 9/20/25 3:00pm | Thorndike Field 1 | Arlington B8 Hurricanes | - | Brookline Man City | |
| 4 | 5665 | 9/27/25 3:00pm | Ryan Connolly Field 11v11 | Winchester United | - | Brookline Man City | |
| 5 | 5669 | 10/4/25 1:30pm | Beaver Country Day School | Brookline Man City | - | Wayland FC | |
| 6 | 5672 | 10/11/25 1:30pm | Beaver Country Day School | Brookline Man City | - | Watertown Warriors | |
| 7 | 5676 | 10/18/25 1:30pm | Lincoln Fields3 | Lexington Minutemen | - | Brookline Man City | |
| 8 | 5679 | 10/25/25 1:30pm | Beaver Country Day School | Brookline Man City | - | Arlington B8 Hurricanes | |
| 9 | 5681 | 11/1/25 1:30pm | Beaver Country Day School | Brookline Man City | - | Winchester United | |
| 10 | 5684 | 11/8/25 3:30pm | High School Turf #4 | Wayland FC | - | Brookline Man City | |
