| 1 | 6346 | 9/6/25 9:00am | Sprague 2 (turf) | Wellesley Storm 8G | 2 - 0 | Winchester Red Stars | |
| 2 | 6349 | 9/13/25 9:00am | Ryan Connolly Field 11v11 | Winchester Red Stars | - | Needham Phoenix | |
| 3 | 6353 | 9/20/25 9:00am | Kennedy Middle School | Natick Electricks | - | Winchester Red Stars | |
| 4 | 6355 | 9/27/25 9:00am | Ryan Connolly Field 11v11 | Winchester Red Stars | - | Medfield Warriors 8G | |
| 5 | 6360 | 10/4/25 9:00am | Beaver Country Day School | Brookline Courage | - | Winchester Red Stars | |
| 6 | 6361 | 10/11/25 9:00am | Ryan Connolly Field 11v11 | Winchester Red Stars | - | Wellesley Storm 8G | |
| 7 | 6365 | 10/18/25 9:00am | DeFazio Field #1 Brock | Needham Phoenix | - | Winchester Red Stars | |
| 8 | 6367 | 10/25/25 9:00am | Ryan Connolly Field 11v11 | Winchester Red Stars | - | Natick Electricks | |
| 9 | 6371 | 11/1/25 9:00am | Wheelock - # 5 | Medfield Warriors 8G | - | Winchester Red Stars | |
| 10 | 6373 | 11/8/25 9:00am | Ryan Connolly Field 11v11 | Winchester Red Stars | - | Brookline Courage | |
