| 1 | 4740 | 9/10/16 9:00am | Milford High School 11v11 GRASS | Milford-Hopedale Chargers | 1 - 4 | Millis United G8 | |
| 2 | 4714 | 9/17/16 9:00am | High School - Obsolete DO NOT USE | Medway Mustangs | 1 - 5 | Milford-Hopedale Chargers | |
| 3 | 4717 | 9/24/16 9:00am | C&S Insurance Field - 1 | Mansfield Hornets | 0 - 3 | Milford-Hopedale Chargers | |
| 4 | 4720 | 11/5/16 9:00am | Milford High School 11v11 GRASS | Milford-Hopedale Chargers | 1 - 1 | Franklin Panthers | Played 11/5 |
| 5 | 4723 | 10/29/16 1:00pm | AFM School | Blackstone UNITED JM | 7 - 1 | Milford-Hopedale Chargers | played 10/29/2016 |
| 6 | 4725 | 10/15/16 9:00am | Oak Grove Farm 11v11 | Millis United G8 | 2 - 3 | Milford-Hopedale Chargers | |
| 7 | 4729 | 10/22/16 9:00am | Milford High School 11v11 GRASS | Milford-Hopedale Chargers | 0 - 0 | Arlington Barry | |
| 8 | 4732 | 10/29/16 9:00am | Milford High School 11v11 GRASS | Milford-Hopedale Chargers | 3 - 0 | Mansfield Hornets | |
| 9 | 4735 | 11/4/16 6:00pm | Franklin HS Front Turf | Franklin Panthers | 0 - 1 | Milford-Hopedale Chargers | |
| 10 | 4738 | 11/12/16 9:00am | Milford High School 11v11 GRASS | Milford-Hopedale Chargers | 1 - 2 | Blackstone UNITED JM | |
