| 1 | 4021 | 4/10/21 9:00am | Millennium Park C | Parkway United | 2 - 0 | Wellesley Pride | |
| 2 | 4024 | 4/17/21 9:00am | Sprague 3 (turf) | Wellesley Pride | 0 - 2 | Hopkinton G8 Academy White | |
| 3 | 4028 | 4/24/21 9:00am | Elm Bank Field 2 | Natick Union | 2 - 1 | Wellesley Pride | |
| 4 | 4030 | 5/1/21 9:00am | Elm Bank 4 | Wellesley Pride | 2 - 1 | Foxboro Warriors 7/8G-2 | |
| 5 | 4035 | 5/8/21 9:00am | Franklin HS Front Turf | Franklin Strikers | 4 - 0 | Wellesley Pride | |
| 6 | 4036 | 6/3/21 6:00pm | Millennium Park C | Parkway United | 1 - 0 | Wellesley Pride | |
| 7 | 4040 | 5/22/21 10:45am | Fruit St. Turf Field 1 | Hopkinton G8 Academy White | 1 - 2 | Wellesley Pride | |
| 8 | 4042 | 5/29/21 9:00am | Cole North (11v11) | Natick Union | 2 - 1 | Wellesley Pride | |
| 9 | 4046 | 6/5/21 9:00am | Hersey-1 (11v11) | Foxboro Warriors 7/8G-2 | 0 - 2 | Wellesley Pride | |
| 10 | 4048 | 6/12/21 9:00am | Elm Bank 4 | Wellesley Pride | 0 - 6 | Franklin Strikers | |
