| 1 | 4711 | 9/11/21 2:30pm | Oak Grove Farm 11v11 | Millis Revolution G8B | 3 - 2 | Milford-Hopedale Fireballs | |
| 2 | 4714 | 9/18/21 2:30pm | Milford HIgh School Turf | Milford-Hopedale Fireballs | 0 - 2 | King Philip PATRIOTS | |
| 3 | 4718 | 9/25/21 4:00pm | HYSA Park M-2 | Holliston B7/8 Scaramella | 4 - 1 | Milford-Hopedale Fireballs | |
| 4 | 4720 | 10/2/21 2:30pm | Milford High School 11v11 GRASS | Milford-Hopedale Fireballs | 1 - 1 | Needham Hammers | |
| 5 | 4725 | Unscheduled | | Framingham Team Amigos | - | Milford-Hopedale Fireballs | |
| 6 | 4726 | 10/16/21 2:30pm | Milford High School 11v11 GRASS | Milford-Hopedale Fireballs | 3 - 2 | Millis Revolution G8B | |
| 7 | 4730 | 10/23/21 9:00am | Freeman Kennedy School - Field H | King Philip PATRIOTS | 5 - 1 | Milford-Hopedale Fireballs | |
| 8 | 4732 | 10/30/21 2:30pm | Milford HIgh School Turf | Milford-Hopedale Fireballs | 2 - 3 | Holliston B7/8 Scaramella | |
| 9 | 4736 | 11/6/21 3:00pm | DeFazio #2 Founders Field | Needham Hammers | 1 - 2 | Milford-Hopedale Fireballs | |
| 10 | 4738 | 11/20/21 10:00am | Milford High School 11v11 GRASS | Milford-Hopedale Fireballs | 2 - 2 | Framingham Team Amigos | |
