| 1 | 6364 | 9/11/21 10:30am | North Field | Medway Mustangs | 6 - 1 | Hopkinton United (B8) | |
| 2 | 6367 | 9/18/21 2:15pm | Fruit St. Turf Field 1 | Hopkinton United (B8) | 1 - 2 | Natick Revolution | |
| 3 | 6372 | 9/25/21 12:30pm | Fruit St. Turf Field 1 | Hopkinton Thunder (B8) | 1 - 5 | Hopkinton United (B8) | |
| 4 | 6374 | 10/2/21 12:30pm | Fruit St. Turf Field 1 | Hopkinton United (B8) | 0 - 5 | Westwood Wild | |
| 5 | 6377 | 10/6/21 6:00pm | Sam Berns Community Field FHS-1 | Foxboro Warriors 7/8B-2 | 7 - 1 | Hopkinton United (B8) | |
| 6 | 6384 | 10/16/21 2:15pm | Fruit St. Turf Field 1 | Hopkinton United (B8) | 3 - 7 | Medway Mustangs | |
| 7 | 6387 | 10/23/21 10:35am | Elm Bank Field 4 | Natick Revolution | 5 - 1 | Hopkinton United (B8) | |
| 8 | 6391 | 10/30/21 2:15pm | Fruit St. Turf Field 1 | Hopkinton United (B8) | 0 - 5 | Wayland United | |
| 9 | 6395 | 11/6/21 1:00pm | DeFazio #2 Founders Field | Needham Defenders | 5 - 0 | Hopkinton United (B8) | |
| 10 | 6398 | 11/13/21 12:30pm | Fruit St. Turf Field 1 | Hopkinton United (B8) | 0 - 6 | Medfield Fire 8B | |
