| 2941 | 4/10/21 9:00am | Elm Bank 3A | Wellesley Wildcats | 0 - 3 | Medfield United 6G | |
| 2946 | 4/17/21 10:30am | Stage Harbor Financial Field - 1B | Mansfield Hornets II | 1 - 1 | Wellesley Wildcats | |
| 2947 | 4/24/21 10:30am | Freeman Kennedy | Norfolk Crew | - | Wellesley Wildcats | |
| 2951 | 5/1/21 10:30am | Elm Bank 3B | Wellesley Wildcats | - | Framingham United | |
| 2954 | 5/8/21 9:00am | Multi-Purpose 9v9 Turf WHS | Westwood Courage | - | Wellesley Wildcats | |
| 2956 | 5/15/21 11:45am | Wheelock - 9v9-2 | Medfield United 6G | - | Wellesley Wildcats | |
| 2959 | 5/22/21 10:30am | Elm Bank 3A | Wellesley Wildcats | - | Mansfield Hornets II | |
| 2963 | 5/29/21 10:30am | | Wellesley Wildcats | - | Norfolk Crew | |
| 2965 | 6/5/21 10:30am | Merchant Road Field 3 | Framingham United | - | Wellesley Wildcats | |
| 2969 | 6/12/21 10:30am | Elm Bank 3B | Wellesley Wildcats | - | Westwood Courage | |
