| 1 | 5613 | 9/11/21 4:30pm | Milton High School Middle Field | Milton Royals | 4 - 4 | Wellesley Warriors | |
| 2 | 5616 | 9/18/21 9:00am | Elm Bank 1 | Wellesley Warriors | 2 - 0 | Wellesley Hawks | |
| 3 | 5619 | 9/25/21 10:30am | Sprague 2 (turf) | Wellesley Warriors | 0 - 4 | Newton G Warriors | |
| 4 | 5622 | 10/2/21 12:00pm | Fessenden A / Class of 1985 | Newton G Breakers | 2 - 1 | Wellesley Warriors | |
| 5 | 5625 | 10/17/21 1:30pm | Elm Bank 2 | Wellesley Warriors | 5 - 0 | D-S Union | |
| 6 | 5628 | 10/16/21 10:30am | Elm Bank 1 | Wellesley Warriors | 2 - 3 | Milton Royals | |
| 7 | 5629 | 10/23/21 9:00am | Elm Bank 1 | Wellesley Hawks | 0 - 1 | Wellesley Warriors | |
| 8 | 5634 | 10/30/21 8:30am | Weeks G | Newton G Warriors | 3 - 1 | Wellesley Warriors | |
| 9 | 5637 | 11/6/21 9:00am | Elm Bank 2 | Wellesley Warriors | 3 - 2 | Newton G Breakers | two confirming emails from coaches |
| 10 | 5638 | 11/13/21 9:00am | Chickering Field | D-S Union | 0 - 5 | Wellesley Warriors | |
