| 1 | 2911 | 10/8/20 7:30pm | Sam Berns Community Field FHS-1 | Foxboro Warriors 7/8G-1 | 0 - 0 | Hopkinton G8 Academy Orange | |
| 2 | 2914 | 9/19/20 9:00am | Fruit St. Turf Field 1 | Hopkinton G8 Academy Orange | 0 - 4 | Milton Breakers | |
| 3 | 2918 | 9/26/20 9:00am | Fessenden Field | D-S Arsenal | 1 - 3 | Hopkinton G8 Academy Orange | |
| 4 | 2920 | 10/3/20 9:00am | Fruit St. Turf Field 1 | Hopkinton G8 Academy Orange | 2 - 3 | Canton United | |
| 5 | 2925 | 10/10/20 9:00am | Ellis 11v11 | Walpole Trouble | 3 - 1 | Hopkinton G8 Academy Orange | |
| 6 | 2926 | 10/17/20 11:45am | Fruit St. Turf Field 1 | Hopkinton G8 Academy Orange | 0 - 5 | Foxboro Warriors 7/8G-1 | |
| 7 | 2930 | 10/24/20 8:30am | Milton High School Middle Field | Milton Breakers | 5 - 3 | Hopkinton G8 Academy Orange | |
| 8 | 2932 | 11/11/20 6:00pm | High School Turf Field | Hopkinton G8 Academy Orange | 0 - 3 | D-S Arsenal | |
| 9 | 2936 | 11/7/20 10:45am | Memorial 11v11 Field (turf) | Canton United | 3 - 3 | Hopkinton G8 Academy Orange | |
| 10 | 2938 | 11/14/20 9:00am | Fruit St. Turf Field 1 | Hopkinton G8 Academy Orange | 0 - 2 | Walpole Trouble | |
