| 1 | 5582 | 9/7/19 9:00am | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 0 - 1 | Medfield Strikers | |
| 2 | 5584 | 9/14/19 9:00am | Franklin HS Front Turf | Franklin Thunder | 3 - 1 | Hopkinton Cheetahs | |
| 3 | 5587 | 9/21/19 10:45am | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 1 - 5 | Franklin Lightning | |
| 4 | 5592 | 9/28/19 12:30pm | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 0 - 2 | Walpole Hurricanes | |
| 5 | 5593 | 10/5/19 9:00am | Milford High School 11v11 GRASS | Milford-Hopedale Strykers United - | 5 - 1 | Hopkinton Cheetahs | |
| 6 | 5597 | 10/12/19 9:00am | Wheelock - # 15 | Medfield Strikers | 3 - 2 | Hopkinton Cheetahs | |
| 7 | 5600 | 10/19/19 12:30pm | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 0 - 3 | Franklin Thunder | |
| 8 | 5603 | 10/26/19 9:00am | Franklin HS Stadium | Franklin Lightning | 1 - 0 | Hopkinton Cheetahs | |
| 9 | 5607 | 11/2/19 10:30am | Milton High School Middle Field | Milton Comets | 0 - 1 | Hopkinton Cheetahs | |
| 10 | 5610 | 11/9/19 12:30pm | Fruit St. Turf Field 1 | Hopkinton Cheetahs | 0 - 1 | Milford-Hopedale Strykers United - | |
