| 1 | 812 | 9/7/19 2:15pm | Fruit St. Grass Field 4B | Hopkinton Revolution | 3 - 0 | Newton B Fire | |
| 2 | 814 | 9/14/19 1:00pm | Alphabet | Weston Lions | 4 - 2 | Hopkinton Revolution | |
| 3 | 817 | 9/21/19 1:00pm | Fruit St. Grass Field 5C | Hopkinton Revolution | 4 - 3 | Natick United | |
| 4 | 822 | 9/28/19 10:00am | Fruit St. Grass Field 4B | Hopkinton Revolution | 1 - 7 | Holliston B4 McDonald/Dupuis | |
| 5 | 823 | 10/5/19 12:00pm | Lynch 7v7-2 | Winchester Warriors | 3 - 1 | Hopkinton Revolution | |
| 6 | 827 | Unscheduled | Wheelock - # 9 | Medfield Warriors | - | Hopkinton Revolution | |
| 7 | 830 | 10/19/19 1:30pm | Fruit St. Grass Field 5D | Hopkinton Revolution | 2 - 4 | Weston Lions | |
| 8 | 833 | 10/26/19 1:00pm | MathWorks Upper (7v7) | Natick United | 5 - 5 | Hopkinton Revolution | |
| 9 | 837 | 11/2/19 2:30pm | Millennium Park C | Parkway United Blue | 3 - 3 | Hopkinton Revolution | |
| 10 | 840 | 11/9/19 1:00pm | Fruit St. Grass Field 5C | Hopkinton Revolution | 5 - 1 | Milford-Hopedale Hawks Caldon | |
