| 1 | 4563 | 9/7/19 2:30pm | Upper Haskell 1 (11v11) | Westborough Real - B8 | 4 - 2 | Hopkinton B8 Academy Orange | |
| 2 | 4566 | 9/14/19 2:15pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 1 - 7 | Marlboro Panthers - B8 3H | Lopsided once again. Marlboro in wrong division. |
| 3 | 4569 | 9/21/19 2:15pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 3 - 0 | Southboro Stars | |
| 4 | 4572 | 9/28/19 2:30pm | Oak Grove Farm 11v11 | Millis United G8B | 2 - 6 | Hopkinton B8 Academy Orange | |
| 5 | 4575 | 10/5/19 2:15pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 0 - 1 | Ashland Revolution | |
| 6 | 4578 | 10/7/19 5:00pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 4 - 2 | Westborough Real - B8 | |
| 7 | 4579 | 10/19/19 4:00pm | Milford High School 11v11 GRASS | Milford-Hopedale Fireballs | 0 - 4 | Hopkinton B8 Academy Orange | |
| 8 | 4584 | 10/26/19 1:00pm | 9/11 Memorial Field | Southboro Stars | 4 - 3 | Hopkinton B8 Academy Orange | |
| 9 | 4587 | 11/2/19 12:30pm | Fruit St. Turf Field 1 | Hopkinton B8 Academy Orange | 7 - 4 | Millis United G8B | |
| 10 | 4588 | 11/9/19 2:00pm | Walker Field | Ashland Revolution | 1 - 1 | Hopkinton B8 Academy Orange | |
