| 1 | 4353 | 9/11/21 3:00pm | Fruit St. Turf Field 1 | Hopkinton Hillers (B8) | 6 - 1 | King Philip Warriors Boys | |
| 2 | 4355 | 9/18/21 12:00pm | Fessenden B/Kumin-Loring | Newton B FC | 0 - 4 | Hopkinton Hillers (B8) | |
| 3 | 4358 | 9/25/21 2:15pm | Fruit St. Turf Field 1 | Hopkinton Hillers (B8) | 1 - 1 | Westborough United - B8 | |
| 4 | 4361 | 10/2/21 1:00pm | Memorial 11v11 Field (turf) | Canton Boys Grade 7/8 United | 2 - 1 | Hopkinton Hillers (B8) | |
| 5 | 4363 | 10/6/21 5:00pm | Fruit St. Turf Field 1 | Hopkinton Hillers (B8) | 3 - 2 | Attleboro Coyotes | |
| 6 | 4368 | 10/16/21 2:30pm | HS Turf Field - Field #1 | Weston United | 8 - 2 | Hopkinton Hillers (B8) | |
| 7 | 4371 | 10/23/21 2:15pm | Fruit St. Turf Field 1 | Hopkinton Hillers (B8) | 4 - 2 | Newton B FC | |
| 8 | 4372 | 11/10/21 8:00pm | New England Baseball Complex Field 1A | Westborough United - B8 | 2 - 3 | Hopkinton Hillers (B8) | |
| 9 | 4375 | 11/17/21 6:00pm | High School Turf Field | Hopkinton Hillers (B8) | 0 - 4 | Canton Boys Grade 7/8 United | |
| 10 | 4380 | 11/13/21 12:00pm | Drummond | Attleboro Coyotes | 0 - 0 | Hopkinton Hillers (B8) | |
