| 1 | 4203 | 9/7/19 3:00pm | Danehy 1 - Artificial Turf | Cambridge FC | 3 - 1 | Arlington Jaguars | |
| 2 | 4206 | 9/14/19 2:00pm | Peirce Field (HS turf) | Arlington Jaguars | 2 - 0 | Newton B City | |
| 3 | 4209 | 9/21/19 2:00pm | Peirce Field (HS turf) | Arlington Jaguars | 2 - 0 | Natick Bolts | |
| 4 | 4212 | 9/28/19 3:00pm | DeFazio Field #1 Brock | Needham United | 2 - 4 | Arlington Jaguars | |
| 5 | 4215 | 10/5/19 1:30pm | Spy Pond Field | Arlington Jaguars | 3 - 4 | Winchester Avalanche | |
| 6 | 4218 | 10/6/19 4:30pm | AC Turf | Arlington Jaguars | 4 - 4 | Cambridge FC | |
| 7 | 4219 | 10/19/19 3:00pm | Fessenden A/Class of 1985 | Newton B City | 2 - 3 | Arlington Jaguars | |
| 8 | 4224 | 10/26/19 2:30pm | Millennium Park C | Parkway United Blue | 4 - 3 | Arlington Jaguars | |
| 9 | 4227 | 11/2/19 2:00pm | Peirce Field (HS turf) | Arlington Jaguars | 1 - 2 | Needham United | |
| 10 | 4228 | 11/9/19 1:30pm | Ryan Connolly Field 11v11 | Winchester Avalanche | 3 - 1 | Arlington Jaguars | |
