| 1 | 4171 | 4/6/19 3:00pm | English High School 11v11 | JP Athletics | 1 - 2 | Wellesley Orient | |
| 2 | 4176 | 4/13/19 3:00pm | Fessenden A/Class of 1985 | Newton B Aces | 4 - 3 | Wellesley Orient | |
| 3 | 4177 | 5/10/19 6:30pm | Danehy 1 - Artificial Turf | Cambridge Falcons | 4 - 0 | Wellesley Orient | |
| 4 | 4181 | 5/22/19 6:30pm | Elm Bank 1 | Wellesley Orient | 3 - 2 | Weston Strikers | |
| 5 | 4184 | 5/4/19 4:00pm | Elm Bank Field 4 | Natick Ravens | 3 - 3 | Wellesley Orient | |
| 6 | 4186 | 5/11/19 4:30pm | Sprague 3 (turf) | Wellesley Orient | 0 - 4 | JP Athletics | |
| 7 | 4189 | 5/18/19 1:30pm | Sprague 3 (turf) | Wellesley Orient | 1 - 2 | Newton B Aces | |
| 8 | 4193 | 6/1/19 1:30pm | Elm Bank 1 | Wellesley Orient | 1 - 1 | Cambridge Falcons | |
| 9 | 4195 | 6/8/19 4:00pm | HS Turf Field - Field #1 | Weston Strikers | 0 - 7 | Wellesley Orient | |
| 10 | 4199 | 6/15/19 3:00pm | Elm Bank 2 | Wellesley Orient | 4 - 5 | Natick Ravens | |
