| 1 | 6738 | 9/6/25 10:45am | Fessenden A / Class of 1985 | Newton G Revolution | - | Wellesley Golden Cleats | |
| 2 | 6741 | 9/13/25 10:30am | Sprague 3 (turf) | Wellesley Golden Cleats | - | Sudbury City | |
| 3 | 6744 | 9/20/25 10:30am | Sprague 2 (turf) | Wellesley Golden Cleats | - | Needham Comets | |
| 4 | 6747 | 9/27/25 9:00am | Byrne (Carisbrooke) | Marlboro Panthers | - | Wellesley Golden Cleats | |
| 5 | 6750 | 10/4/25 10:30am | Sprague 3 (turf) | Wellesley Golden Cleats | - | Natick Union | |
| 6 | 6753 | 10/11/25 9:00am | | Wellesley Golden Cleats | - | Newton G Revolution | |
| 7 | 6754 | 10/18/25 9:00am | Lincoln Sudbury Regional High School | Sudbury City | - | Wellesley Golden Cleats | |
| 8 | 6759 | 10/25/25 1:00pm | DeFazio Field #1 Brock | Needham Comets | - | Wellesley Golden Cleats | |
| 9 | 6762 | 11/1/25 9:00am | Sprague 2 (turf) | Wellesley Golden Cleats | - | Marlboro Panthers | |
| 10 | 6763 | 11/8/25 9:00am | Kennedy Middle School | Natick Union | - | Wellesley Golden Cleats | |
