| 1 | 61 | 4/6/19 10:30am | Upper Haskell 4 (7v7) | Westborough United - B3 | 6 - 3 | Wayland Warriors | |
| 2 | 66 | 4/20/19 4:00pm | Plymouth Street 12 | Mansfield White Hornets | 1 - 1 | Wayland Warriors | Play by 05May19 |
| 3 | 67 | 4/20/19 2:30pm | FieldHouse Arena - 10 | Mansfield Green Hornets | 2 - 1 | Wayland Warriors | |
| 4 | 71 | 4/27/19 10:30am | Claypit Hill #7 | Wayland Warriors | 3 - 3 | Milford-Hopedale Hawks Grade 3 | |
| 5 | 74 | 5/4/19 1:00pm | Forekicks 2 (Field 3) - INSIDE | Southboro Galaxy | 1 - 2 | Wayland Warriors | |
| 6 | 76 | 5/11/19 2:30pm | Claypit Hill #11 | Wayland Warriors | 1 - 3 | Natick United | Relocating to Wayland |
| 7 | 79 | 5/18/19 10:30am | Claypit Hill #11 | Wayland Warriors | 4 - 2 | Mansfield White Hornets | |
| 8 | 83 | 6/1/19 10:30am | Claypit Hill #11 | Wayland Warriors | 4 - 1 | Mansfield Green Hornets | |
| 9 | 85 | 6/8/19 2:30pm | Plains Park 7v7 Field #1 | Milford-Hopedale Hawks Grade 3 | 2 - 7 | Wayland Warriors | |
| 10 | 89 | 6/15/19 10:30am | Claypit Hill #11 | Wayland Warriors | 5 - 0 | Southboro Galaxy | |
