| 1 | 4711 | 9/7/19 2:30pm | Wayland Middle School #3 | Wayland United | 11 - 0 | Hopkinton Warriors | no roster for Hopkinton |
| 2 | 4714 | 9/14/19 4:00pm | Fruit St. Turf Field 1 | Hopkinton Warriors | 0 - 8 | Ashland Wolves | |
| 3 | 4718 | 9/21/19 2:30pm | Ellsworth-McAfee Field C | Northborough Dynamoes | 10 - 2 | Hopkinton Warriors | |
| 4 | 6655 | 9/28/19 1:00pm | Franklin HS Front Turf | Franklin Thunder | 3 - 1 | Hopkinton Warriors | |
| 5 | 6659 | 10/5/19 12:30pm | Fruit St. Turf Field 1 | Hopkinton Warriors | 1 - 7 | Franklin Lightning | |
| 6 | 6661 | 10/12/19 10:45am | Fruit St. Turf Field 1 | Hopkinton Warriors | 2 - 4 | Attleboro Crew | |
| 7 | 6666 | 10/19/19 10:45am | King Philip Middle School- Field 1 | King Philip FIRE-B | 5 - 0 | Hopkinton Warriors | |
| 8 | 6670 | 10/26/19 12:30pm | Fruit St. Turf Field 1 | Hopkinton Warriors | 2 - 5 | Walpole Coyotes | |
| 9 | 6675 | 11/2/19 2:15pm | Fruit St. Turf Field 1 | Hopkinton Warriors | 1 - 3 | Walpole Pirates | |
| 10 | 6677 | Unscheduled | Sam Berns Community Field FHS-1 | Foxboro NEW | - | Hopkinton Warriors | |
