| 1 | 4473 | 9/7/19 2:30pm | Franklin HS Stadium | Franklin United | 1 - 4 | Mansfield Hornets II | |
| 2 | 4476 | 9/14/19 4:00pm | C&S Insurance Field - 1 | Mansfield Hornets II | 3 - 0 | Hopkinton Hillers | |
| 3 | 4479 | 9/21/19 4:00pm | C&S Insurance Field - 1 | Mansfield Hornets II | 4 - 0 | North Attleboro Rockets 7/8 RA | |
| 4 | 4482 | 9/28/19 2:30pm | HYSA Park M-3 | Holliston B7/8 Maloney | 0 - 5 | Mansfield Hornets II | |
| 5 | 4485 | 10/5/19 4:00pm | C&S Insurance Field - 1 | Mansfield Hornets II | 1 - 9 | Marlboro Panthers - B8 3H | |
| 6 | 4488 | 11/16/19 1:30pm | C&S Insurance Field - 1 | Mansfield Hornets II | 2 - 1 | Franklin United | |
| 7 | 4489 | 10/19/19 3:30pm | Fruit St. Turf Field 1 | Hopkinton Hillers | 0 - 5 | Mansfield Hornets II | |
| 8 | 4372 | 10/26/19 2:30pm | Upper Haskell 1 (11v11) | Westborough United - B8 | 6 - 1 | Mansfield Hornets II | |
| 9 | 4375 | 11/2/19 4:00pm | C&S Insurance Field - 1 | Mansfield Hornets II | 0 - 1 | Norwood Revolution | |
| 10 | 4380 | 11/9/19 2:30pm | Wheelock - # 10 | Medfield United | 3 - 0 | Mansfield Hornets II | |
