| 1 | 61 | 9/7/19 2:15pm | Fruit St. Grass Field 5C | Hopkinton Galaxy | 1 - 1 | Natick Phoenix | |
| 2 | 66 | 9/14/19 2:30pm | Haskell | Sudbury Warriors | 8 - 6 | Hopkinton Galaxy | |
| 3 | 67 | 9/21/19 2:30pm | PJ Shannon Remodeling Field - 31 | Mansfield Green Hornets | 2 - 6 | Hopkinton Galaxy | |
| 4 | 71 | 9/28/19 12:15pm | Fruit St. Grass Field 5D | Hopkinton Galaxy | 2 - 1 | Westborough United - B3 | |
| 5 | 74 | 10/5/19 2:30pm | PJ Shannon Remodeling Field - 31 | Mansfield White Hornets | 1 - 6 | Hopkinton Galaxy | |
| 6 | 76 | 10/12/19 12:00pm | Soule Recreation Center | Brookline Red Bulls | 4 - 2 | Hopkinton Galaxy | |
| 7 | 79 | 10/19/19 2:15pm | Fruit St. Grass Field 5C | Hopkinton Galaxy | 6 - 3 | Sudbury Warriors | |
| 8 | 83 | 10/26/19 2:15pm | Fruit St. Grass Field 5C | Hopkinton Galaxy | 2 - 1 | Mansfield Green Hornets | |
| 9 | 85 | 11/2/19 2:30pm | Chauncey 4 (7v7) | Westborough United - B3 | 5 - 3 | Hopkinton Galaxy | |
| 10 | 89 | 11/9/19 2:15pm | Fruit St. Grass Field 5C | Hopkinton Galaxy | 2 - 5 | Hill House United | |
