| 1 | 3481 | 9/8/18 4:00pm | Weeks B | Newton B Liverpool | 2 - 4 | Cambridge Rovers | |
| 2 | 3485 | 9/15/18 4:00pm | Danehy 2 - artificial turf | Cambridge Rovers | 2 - 1 | Arlington Marauders | |
| 3 | 3488 | 9/22/18 1:00pm | Pagel Field | JP Forza JP | 1 - 10 | Cambridge Rovers | |
| 4 | 3489 | 9/29/18 1:30pm | McClennen Park 1 | Arlington Cyclones | 1 - 0 | Cambridge Rovers | |
| 5 | 3493 | 10/6/18 4:00pm | Danehy 2 - artificial turf | Cambridge Rovers | 0 - 3 | Bedford United | |
| 6 | 3496 | 10/13/18 2:00pm | Danehy 2 - artificial turf | Cambridge Rovers | 2 - 2 | Newton B Liverpool | |
| 7 | 3500 | 10/20/18 1:30pm | McClennen Park 1 | Arlington Marauders | 0 - 0 | Cambridge Rovers | |
| 8 | 3503 | 11/4/18 3:00pm | Danehy 1 - Artificial Turf | Cambridge Rovers | 4 - 1 | Arlington Hawks | |
| 9 | 3504 | 11/3/18 12:00pm | Danehy 1 - Artificial Turf | Cambridge Rovers | 5 - 2 | Arlington Cyclones | |
| 10 | 3508 | 11/10/18 1:00pm | HYSA Park M-2 | Holliston B5/6 Malvey | 1 - 4 | Cambridge Rovers | |
