| 1 | 4321 | 9/7/19 2:00pm | Peirce Field (HS turf) | Arlington Pond Sharks | 3 - 3 | Weston United | |
| 2 | 4326 | 9/14/19 12:00pm | Fessenden A/Class of 1985 | Newton B SOCA WARRIORS | 3 - 2 | Arlington Pond Sharks | |
| 3 | 4327 | 9/21/19 1:30pm | Sprague 3 (turf) | Wellesley Heat | 3 - 2 | Arlington Pond Sharks | |
| 4 | 4331 | 9/28/19 2:00pm | Peirce Field (HS turf) | Arlington Pond Sharks | 4 - 4 | Milton Vipers | |
| 5 | 4334 | 10/5/19 3:00pm | Lincoln Fields1 | Lexington Gunners | 2 - 0 | Arlington Pond Sharks | |
| 6 | 4336 | 10/20/19 10:00am | Proctor | Weston United | 3 - 0 | Arlington Pond Sharks | Postponed Make Date TBA |
| 7 | 4339 | 10/19/19 2:00pm | Peirce Field (HS turf) | Arlington Pond Sharks | 1 - 2 | Newton B SOCA WARRIORS | |
| 8 | 4343 | 10/26/19 2:00pm | Peirce Field (HS turf) | Arlington Pond Sharks | 1 - 1 | Wellesley Heat | |
| 9 | 4345 | 11/2/19 2:30pm | Milton High School Middle Field | Milton Vipers | 5 - 0 | Arlington Pond Sharks | |
| 10 | 4349 | 11/9/19 2:00pm | Peirce Field (HS turf) | Arlington Pond Sharks | 0 - 1 | Lexington Gunners | |
