| 1 | 3833 | Unscheduled | | Wellesley Raiders | - | Wayland United | |
| 2 | 3837 | 9/19/20 4:30pm | Downes Field (oval) | Brookline Inter | 3 - 5 | Wellesley Raiders | |
| 3 | 3842 | 9/26/20 3:00pm | Elm Bank 4 | Wellesley Raiders | 1 - 7 | Natick Blazers | |
| 4 | 3847 | 10/3/20 5:00pm | Center Track Field | Lexington Bears | 7 - 1 | Wellesley Raiders | |
| 5 | 3851 | 10/10/20 1:30pm | Sprague 2 (turf) | Wellesley Raiders | 2 - 5 | Newton B Revolution | |
| 6 | 3858 | 10/17/20 3:30pm | High School Turf #4 | Wayland United | 6 - 1 | Wellesley Raiders | |
| 7 | 3863 | 10/24/20 3:00pm | Elm Bank 4 | Wellesley Raiders | 1 - 6 | Brookline Inter | |
| 8 | 3866 | 11/11/20 7:15pm | High School - Varsity Field (grass) | Natick Blazers | 5 - 0 | Wellesley Raiders | |
| 9 | 3871 | 11/7/20 3:00pm | Sprague 2 (turf) | Wellesley Raiders | 1 - 7 | Lexington Bears | |
| 10 | 3878 | 11/14/20 3:00pm | Fessenden A/Class of 1985 | Newton B Revolution | 4 - 1 | Wellesley Raiders | |
