| 1 | 4412 | 4/6/19 4:00pm | PQ (1A) | Belmont B8-4 Rams | 0 - 4 | Wellesley Razorbacks | |
| 2 | 4414 | 4/13/19 12:00pm | Ryan Connolly Field 11v11 | Winchester Lions | 3 - 0 | Wellesley Razorbacks | |
| 3 | 4417 | 4/20/19 3:00pm | Sprague 2 (turf) | Wellesley Razorbacks | 1 - 0 | Arlington Bobcats | |
| 4 | 4422 | 5/19/19 12:00pm | Danehy 2 - artificial turf | Cambridge Strikers | 1 - 4 | Wellesley Razorbacks | |
| 5 | 4423 | 5/4/19 2:30pm | Pope John Paul II Park | Dorchester Pythons | 1 - 1 | Wellesley Razorbacks | |
| 6 | 4427 | 5/11/19 3:00pm | Sprague 3 (turf) | Wellesley Razorbacks | 3 - 3 | Belmont B8-4 Rams | |
| 7 | 4430 | 5/18/19 1:30pm | Elm Bank 2 | Wellesley Razorbacks | 1 - 1 | Winchester Lions | |
| 8 | 4433 | 6/1/19 1:30pm | Thorndike Field 1 | Arlington Bobcats | 0 - 4 | Wellesley Razorbacks | |
| 9 | 4437 | 6/8/19 3:30pm | Danehy 2 - artificial turf | Cambridge Strikers | 1 - 0 | Wellesley Razorbacks | |
| 10 | 4440 | 6/15/19 3:00pm | Sprague 3 (turf) | Wellesley Razorbacks | 4 - 2 | Dorchester Pythons | |
