| 1 | 4711 | 9/7/19 2:30pm | Wayland Middle School #3 | Wayland United | 11 - 0 | Hopkinton Warriors | no roster for Hopkinton |
| 2 | 4716 | 9/14/19 2:30pm | Whitcomb Middle School Turf | Marlboro Panthers - B8 4C | 3 - 1 | Wayland United | |
| 3 | 4717 | 9/21/19 3:45pm | Walker Field | Ashland Wolves | 1 - 0 | Wayland United | |
| 4 | 4721 | 9/28/19 2:30pm | Wayland Middle School #3 | Wayland United | 2 - 1 | Northborough Dynamoes | |
| 5 | 4724 | 10/5/19 2:30pm | HYSA Park M-3 | Holliston B7/8 Pirelli Panthers | 0 - 3 | Wayland United | |
| 6 | 4726 | 10/19/19 10:00am | Hadley 1 (11v11) | Westborough Barcelona - B8 | 2 - 1 | Wayland United | |
| 7 | 4729 | 10/19/19 2:30pm | Wayland Middle School #3 | Wayland United | 0 - 2 | Marlboro Panthers - B8 4C | |
| 8 | 4733 | 10/26/19 4:00pm | Town Building #1 | Wayland United | 1 - 3 | Ashland Wolves | |
| 9 | 4735 | 11/2/19 2:30pm | Ellsworth-McAfee Field C | Northborough Dynamoes | 0 - 4 | Wayland United | |
| 10 | 4739 | 11/9/19 2:30pm | Wayland Middle School #3 | Wayland United | 1 - 1 | Holliston B7/8 Pirelli Panthers | |
