| 1 | 6927 | 9/7/19 3:00pm | AC Turf | Arlington Bobcats | 0 - 2 | A-B City | |
| 2 | 6931 | 9/14/19 3:00pm | Sprague 3 (turf) | Wellesley Razorbacks | 4 - 2 | Arlington Bobcats | |
| 3 | 6936 | 9/21/19 3:00pm | Spy Pond Field | Arlington Bobcats | 4 - 3 | Natick Revolution | |
| 4 | 6943 | 9/28/19 3:00pm | AC Turf | Arlington Bobcats | 2 - 1 | Newton B Barcelona | |
| 5 | 6946 | 10/5/19 2:00pm | DeFazio #2 Founders Field | Needham Predators | 1 - 2 | Arlington Bobcats | |
| 6 | 6952 | 10/12/19 1:30pm | Lower Fields 2 | A-B City | 3 - 1 | Arlington Bobcats | |
| 7 | 6957 | 10/19/19 3:00pm | AC Turf | Arlington Bobcats | 1 - 1 | Wellesley Razorbacks | |
| 8 | 6962 | 10/26/19 2:30pm | High School - Varsity Field (grass) | Natick Revolution | 1 - 1 | Arlington Bobcats | |
| 9 | 6968 | 11/2/19 1:30pm | Spy Pond Field | Arlington Warriors | 5 - 2 | Arlington Bobcats | |
| 10 | 6973 | 11/9/19 3:00pm | AC Turf | Arlington Bobcats | 1 - F | Needham Predators | Needham forfeited game |
