| 1 | 4201 | 4/10/21 11:15am | Poncin Hewitt | Attleboro United | 1 - 0 | Hopkinton Cheetahs | |
| 2 | 4204 | 4/17/21 10:45am | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 0 - 0 | Franklin United | |
| 3 | 4208 | 4/24/21 9:00am | PJ Shannon Remodeling Field - 31 | Mansfield Hornets IV | 3 - 1 | Hopkinton Cheetahs | |
| 4 | 4210 | 5/1/21 10:45am | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 0 - 2 | North Attleboro Stars 8 | |
| 5 | 4215 | 5/8/21 12:30pm | King Philip Middle School- Field 1 | King Philip Fire | 5 - 0 | Hopkinton Cheetahs | |
| 6 | 4216 | 5/15/21 10:45am | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 0 - 0 | Attleboro United | |
| 7 | 4220 | 5/22/21 9:00am | Beaver Pond/Chilson Beach | Franklin United | 1 - 1 | Hopkinton Cheetahs | |
| 8 | 4222 | 5/29/21 10:00am | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 1 - 3 | Mansfield Hornets IV | |
| 9 | 4226 | 6/5/21 10:30am | Beaupre Field | North Attleboro Stars 8 | 4 - 0 | Hopkinton Cheetahs | |
| 10 | 4228 | 6/12/21 10:45am | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 0 - 1 | Walpole Crusaders | |
