| 1 | 6227 | 9/6/25 3:00pm | Elm Bank 3 | Wellesley Red Wolves | 1 - 1 | Milton Dynamo | |
| 2 | 6229 | 9/13/25 1:00pm | English High School 11v11 | JP Wolves | - | Wellesley Red Wolves | |
| 3 | 6232 | 9/20/25 12:00pm | Sprague 2 (turf) | Wellesley Red Wolves | - | Westwood Coyotes | |
| 4 | 6237 | 9/27/25 3:00pm | Elm Bank 4 | Wellesley Red Wolves | - | Milton Metrostars | |
| 5 | 6238 | 10/4/25 1:30pm | Sprague 2 (turf) | Wellesley FC | - | Wellesley Red Wolves | |
| 6 | 6242 | 10/11/25 3:30pm | Milton High School Middle Field | Milton Dynamo | - | Wellesley Red Wolves | |
| 7 | 6245 | 10/18/25 3:00pm | Sprague 2 (turf) | Wellesley Red Wolves | - | JP Wolves | |
| 8 | 6248 | 10/25/25 12:00pm | Flahive Field HS Turf | Westwood Coyotes | - | Wellesley Red Wolves | |
| 9 | 6252 | 11/1/25 1:45pm | Milton High School Middle Field | Milton Metrostars | - | Wellesley Red Wolves | |
| 10 | 6255 | 11/8/25 12:00pm | Elm Bank 3 | Wellesley Red Wolves | - | Wellesley FC | |
