| 1 | 3483 | 4/10/21 3:30pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 1 - 5 | Millis Galaxy G8B | |
| 2 | 3485 | 4/17/21 2:15pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 0 - 2 | Southboro Stars | |
| 3 | 3488 | 4/26/21 6:00pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 4 - 2 | Holliston B7/8 Morelli | Game Moved to 4/26 |
| 4 | 3491 | 5/1/21 10:30am | North Field | Medway Mustangs | 2 - 0 | Hopkinton B8 Academy Orange | |
| 5 | 3493 | 5/8/21 4:00pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 1 - 5 | Ashland Wolves | |
| 6 | 3498 | 5/15/21 4:00pm | Oak Grove Farm 11v11 | Millis Galaxy G8B | 3 - 3 | Hopkinton B8 Academy Orange | |
| 7 | 3501 | 5/22/21 3:00pm | 9/11 Memorial Field | Southboro Stars | 3 - 3 | Hopkinton B8 Academy Orange | |
| 8 | 3502 | 5/29/21 2:45pm | HYSA Park M-2 | Holliston B7/8 Morelli | 2 - 2 | Hopkinton B8 Academy Orange | |
| 9 | 3505 | 6/5/21 4:00pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 4 - 0 | Needham Hammers | |
| 10 | 3510 | 6/12/21 2:00pm | Walker Field | Ashland Wolves | 5 - 3 | Hopkinton B8 Academy Orange | |
