| 1 | 960 | 9/8/18 1:00pm | Fruit St. Grass Field 5D | Hopkinton Hopkinton FC | 1 - 3 | Milford-Hopedale Jr. Hawks | |
| 2 | 934 | 9/15/18 1:00pm | Claypit Hill #5 | Wayland Warriors | 5 - 0 | Hopkinton Hopkinton FC | |
| 3 | 937 | 9/22/18 1:00pm | 4B 7v7 | Bellingham Blackhawks | 4 - 5 | Hopkinton Hopkinton FC | |
| 4 | 940 | 9/29/18 1:00pm | Fruit St. Grass Field 5D | Hopkinton Hopkinton FC | 3 - 5 | Ashland Pumas | |
| 5 | 943 | 9/30/18 11:15am | Merchant Road Field 5 | Framingham Power | 1 - 0 | Hopkinton Hopkinton FC | |
| 6 | 945 | 10/17/18 5:00pm | Plains Park 7v7 Field #4 | Milford-Hopedale Jr. Hawks | 5 - 0 | Hopkinton Hopkinton FC | |
| 7 | 949 | 10/20/18 1:00pm | Fruit St. Grass Field 5D | Hopkinton Hopkinton FC | 1 - 3 | Wayland Warriors | |
| 8 | 952 | 11/2/18 4:30pm | Fruit St. Grass Field 5D | Hopkinton Hopkinton FC | 0 - 2 | Norfolk Sounders | |
| 9 | 955 | 11/11/18 11:00am | Briasco Field | Ashland Pumas | 6 - 1 | Hopkinton Hopkinton FC | |
| 10 | 958 | 11/10/18 12:15pm | Fruit St. Grass Field 5C | Hopkinton Hopkinton FC | 4 - 2 | Framingham Power | |
