| 1 | 2761 | 9/6/25 1:30pm | Field House Indoor 9v9-Front | Winchester Eagles | 0 - 4 | Parkway B5 United Blue | |
| 2 | 2766 | 9/13/25 11:00am | Friends 1 (9v9) | Foxboro Warriors 5B-Blue | - | Winchester Eagles | |
| 3 | 2767 | 9/20/25 3:00pm | Mylod 2 | Walpole Arsenal | - | Winchester Eagles | |
| 4 | 2771 | 9/27/25 1:30pm | Field House Indoor 9v9-Front | Winchester Eagles | - | Milton Red Storm | |
| 5 | 2774 | 10/4/25 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | - | Winchester Eagles | |
| 6 | 2776 | 10/11/25 1:00pm | Millennium Park C | Parkway B5 United Blue | - | Winchester Eagles | |
| 7 | 2779 | 10/18/25 1:30pm | Field House Indoor 9v9-Front | Winchester Eagles | - | Foxboro Warriors 5B-Blue | |
| 8 | 2783 | 10/25/25 1:30pm | Field House Indoor 9v9-Front | Winchester Eagles | - | Walpole Arsenal | |
| 9 | 2785 | 11/1/25 2:40pm | Andrews Field | Milton Red Storm | - | Winchester Eagles | |
| 10 | 2789 | 11/8/25 1:30pm | Field House Indoor 9v9-Front | Winchester Eagles | - | Canton Boys Grade 5 United | |
