| 1 | 3883 | 9/6/25 2:00pm | High School #12 JV Soccer field next to Softball field | Wayland Thunder | 3 - 2 | Wellesley Hornets 5B | |
| 2 | 3887 | 9/13/25 1:30pm | Bates 2 | Wellesley United | - | Wellesley Hornets 5B | |
| 3 | 3891 | 9/20/25 12:00pm | Bates 1 | Wellesley Hornets 5B | - | Lexington Wolves | |
| 4 | 3893 | 9/27/25 12:00pm | Bates 1 | Wellesley Hornets 5B | - | Winchester Whitecaps | |
| 5 | 3900 | 10/4/25 1:30pm | Field House Indoor 9v9-Back | Winchester Rapids | - | Wellesley Hornets 5B | |
| 6 | 3903 | 10/11/25 1:00pm | | Wellesley Hornets 5B | - | Wayland Thunder | |
| 7 | 3907 | 10/18/25 12:00pm | Sprague 2A | Wellesley Hornets 5B | - | Wellesley United | |
| 8 | 3912 | 10/25/25 1:30pm | Lincoln Fields2 | Lexington Wolves | - | Wellesley Hornets 5B | |
| 9 | 3914 | 11/1/25 1:30pm | Hills Hill Field | Arlington B5 Huskies | - | Wellesley Hornets 5B | |
| 10 | 3917 | 11/8/25 1:30pm | Bates 1 | Wellesley Hornets 5B | - | Arlington B5 Greyhounds | |
