| 1 | 5281 | 9/7/19 10:45am | Fruit St. Turf Field 1 | Hopkinton G8 Academy Orange | 1 - 3 | Newton G Bulldogs | |
| 2 | 5286 | 9/14/19 9:00am | Town Building #1 | Wayland Raiders | 3 - 2 | Hopkinton G8 Academy Orange | |
| 3 | 5287 | 9/21/19 9:00am | PQ (1A) | Belmont G8-2 Cyclones | 1 - 3 | Hopkinton G8 Academy Orange | |
| 4 | 5291 | 9/28/19 10:45am | Fruit St. Turf Field 1 | Hopkinton G8 Academy Orange | 6 - 0 | C-C Charge | |
| 5 | 5294 | 10/5/19 10:30am | Lincoln Sudbury Regional High School | Sudbury Gunners | 3 - 2 | Hopkinton G8 Academy Orange | |
| 6 | 5296 | 11/8/19 5:00pm | Forte 9v9 | Newton G Bulldogs | 1 - 0 | Hopkinton G8 Academy Orange | |
| 7 | 5299 | 10/19/19 10:45am | Fruit St. Turf Field 1 | Hopkinton G8 Academy Orange | 1 - 4 | Wayland Raiders | |
| 8 | 5303 | 10/26/19 9:00am | Fruit St. Turf Field 1 | Hopkinton G8 Academy Orange | 2 - 1 | Belmont G8-2 Cyclones | |
| 9 | 5305 | 11/2/19 9:00am | Cricket Field #1 | Needham Jaguars | 3 - 2 | Hopkinton G8 Academy Orange | |
| 10 | 5309 | 11/9/19 12:00pm | Fruit St. Turf Field 2 | Hopkinton G8 Academy Orange | 0 - 2 | Sudbury Gunners | |
