| 1 | 2867 | 9/9/23 1:30pm | Field House Indoor 9v9-Back | Winchester Eagles | 4 - 1 | Wayland Warriors | |
| 2 | 2870 | 9/16/23 1:00pm | Alpine Field #2 | Wayland Warriors | 3 - 1 | Westborough Real - B5 | |
| 3 | 2874 | 9/23/23 1:00pm | Davis School | Bedford FC | 0 - 1 | Wayland Warriors | |
| 4 | 2875 | 10/14/23 9:00am | Hills Hill Field | Arlington Leopards | 2 - 4 | Wayland Warriors | |
| 5 | 2879 | 10/7/23 1:00pm | Alpine Field #2 | Wayland Warriors | 4 - 5 | Belmont B5 Sounders | |
| 6 | 2882 | 10/14/23 1:00pm | Alpine Field #2 | Wayland Warriors | 0 - 2 | Winchester Eagles | |
| 7 | 2886 | 10/25/23 5:00pm | Chauncey 1 (9v9) | Westborough Real - B5 | 2 - 1 | Wayland Warriors | |
| 8 | 2889 | 10/28/23 1:00pm | Alpine Field #2 | Wayland Warriors | 2 - 1 | Bedford FC | |
| 9 | 2891 | 11/4/23 1:00pm | High School #12 JV Soccer field next to Softball field | Wayland Warriors | 0 - 6 | Arlington Tigers | |
| 10 | 2894 | 11/11/23 4:00pm | Grove St. (1B) | Belmont B5 Sounders | 1 - 1 | Wayland Warriors | |
