| 1 | 4143 | 9/7/19 11:30am | Fruit St. Turf Field 2B | Hopkinton G6 Academy Green | 0 - 0 | Sudbury Stars | |
| 2 | 4145 | 9/14/19 10:30am | HYSA Park M-3 | Holliston G6 Kaufman Panthers | 6 - 0 | Hopkinton G6 Academy Green | |
| 3 | 4148 | 9/21/19 11:30am | Fruit St. Turf Field 2B | Hopkinton G6 Academy Green | 0 - 2 | Holliston G6 TMalvey | |
| 4 | 4151 | 9/28/19 10:30am | Multi-Purpose 9v9 Turf WHS | Westwood Green Gremlins | 0 - 3 | Hopkinton G6 Academy Green | |
| 5 | 4153 | 10/5/19 10:45am | Fruit St. Turf Field 2B | Hopkinton G6 Academy Green | 2 - 5 | Newton G Mountain Lions | |
| 6 | 4158 | 10/20/19 9:00am | Haskell | Sudbury Stars | 1 - 3 | Hopkinton G6 Academy Green | Rescheduled to 10/20 |
| 7 | 4161 | 10/19/19 10:45am | Fruit St. Turf Field 2A | Hopkinton G6 Academy Green | 4 - 1 | Canton Breakers | |
| 8 | 4162 | 10/26/19 9:00am | Weston Pond W-5 | Holliston G6 TMalvey | 3 - 2 | Hopkinton G6 Academy Green | |
| 9 | 4165 | 11/2/19 10:30am | Fruit St. Turf Field 2A | Hopkinton G6 Academy Green | 1 - 0 | Westwood Green Gremlins | |
| 10 | 4170 | 11/9/19 10:30am | Hamilton 1 | Newton G Mountain Lions | X - X | Hopkinton G6 Academy Green | Game Cancelled |
