| 1 | 2101 | 9/21/20 5:30pm | Fruit St. Turf Field 2B | Hopkinton G6 Academy Orange | 1 - 3 | Wayland Nuttmeggers | |
| 2 | 2104 | 9/19/20 11:00am | Alpine Field #2 | Wayland Nuttmeggers | 3 - 1 | Lexington United Jaguars | |
| 3 | 2108 | 10/12/20 5:00pm | Bates 1 | Wellesley Breakaways | 3 - 0 | Wayland Nuttmeggers | |
| 4 | 2110 | 10/3/20 11:00am | Alpine Field #2 | Wayland Nuttmeggers | 0 - 3 | Natick Storm | |
| 5 | 2115 | 10/10/20 10:00am | Weeks E | Newton G Elements | 1 - 1 | Wayland Nuttmeggers | |
| 6 | 2116 | 11/8/20 9:00am | Claypit Hill #8 | Wayland Nuttmeggers | 1 - 1 | Hopkinton G6 Academy Orange | |
| 7 | 2120 | 10/24/20 1:00pm | Lincoln Fields2 | Lexington United Jaguars | 0 - 1 | Wayland Nuttmeggers | |
| 8 | 2122 | 11/4/20 7:30pm | High School Turf #4 | Wayland Nuttmeggers | 3 - 0 | Wellesley Breakaways | |
| 9 | 2126 | 11/7/20 10:30am | Cole North A (9v9) | Natick Storm | 3 - 1 | Wayland Nuttmeggers | |
| 10 | 2128 | 11/14/20 9:00am | Alpine Field #2 | Wayland Nuttmeggers | 1 - 1 | Newton G Elements | |
