| 1 | 2641 | 9/6/25 12:00pm | Field House Indoor 9v9-Front | Winchester Galaxy | 1 - 3 | Westwood Goal Dragons | |
| 2 | 2646 | 9/13/25 1:30pm | Lower Fields 1B | A-B FC | - | Winchester Galaxy | |
| 3 | 2647 | 9/20/25 1:00pm | Ellsworth-McAfee Field D | Northborough Maroon Boys 5 | - | Winchester Galaxy | |
| 4 | 2651 | 9/27/25 12:00pm | Field House Indoor 9v9-Front | Winchester Galaxy | - | Natick United | |
| 5 | 2654 | 10/4/25 1:30pm | McClennen Park 2 | Arlington B5 Bulldogs | - | Winchester Galaxy | |
| 6 | 2656 | 10/11/25 1:00pm | Thurston Upper 9v9 | Westwood Goal Dragons | - | Winchester Galaxy | |
| 7 | 2659 | 10/18/25 12:00pm | Field House Indoor 9v9-Front | Winchester Galaxy | - | A-B FC | |
| 8 | 2663 | 10/25/25 12:00pm | Field House Indoor 9v9-Front | Winchester Galaxy | - | Northborough Maroon Boys 5 | |
| 9 | 2665 | 11/1/25 11:40am | Cole North A (9v9) | Natick United | - | Winchester Galaxy | |
| 10 | 2669 | 11/8/25 12:00pm | Field House Indoor 9v9-Front | Winchester Galaxy | - | Arlington B5 Bulldogs | |
