| 1 | 5481 | 9/9/23 12:45pm | Fruit St. Turf Field 1 | Hopkinton Hurricanes (B8) | 0 - 7 | Framingham Force | |
| 2 | 5486 | 9/16/23 12:10pm | Kennedy Middle School | Natick Cyclones | 4 - 0 | Hopkinton Hurricanes (B8) | |
| 3 | 5487 | 9/23/23 2:30pm | Upper Haskell 1 (11v11) | Westborough Real - B8 | 5 - 0 | Hopkinton Hurricanes (B8) | |
| 4 | 5491 | 9/30/23 2:00pm | Fruit St. Turf Field 1 | Hopkinton Hurricanes (B8) | 0 - 6 | Wayland Warriors | |
| 5 | 5494 | 10/7/23 2:30pm | Ellsworth-McAfee Field A | Northborough Green (Boys 7/8) | 5 - 0 | Hopkinton Hurricanes (B8) | |
| 6 | 5677 | 11/5/23 2:30pm | Fruit St. Turf Field 1 | Hopkinton Hurricanes (B8) | 3 - 1 | Newton B Manchester United | |
| 7 | 5681 | 10/21/23 12:10pm | Elm Bank Field 1 | Natick Revolution | 1 - 1 | Hopkinton Hurricanes (B8) | |
| 8 | 5684 | 10/28/23 1:45pm | Fruit St. Turf Field 1 | Hopkinton Hurricanes (B8) | 1 - 4 | Westwood Hotspur | |
| 9 | 5686 | 11/4/23 12:00pm | Fruit St. Turf Field 1 | Hopkinton Hurricanes (B8) | 0 - 0 | D-S Force | |
| 10 | 5689 | 11/11/23 3:00pm | Hadley 1 (11v11) | Westborough Barcelona - B8 | 2 - 2 | Hopkinton Hurricanes (B8) | |
