| 1 | 3303 | 9/7/19 2:15pm | Fruit St. Turf Field 2A | Hopkinton B6 Academy Orange | 1 - 3 | Attleboro Blue Lightning | |
| 2 | 3305 | 9/14/19 2:30pm | 4C (9v9) | Bellingham Hawks | 5 - 6 | Hopkinton B6 Academy Orange | |
| 3 | 3308 | 9/21/19 2:30pm | Fruit St. Turf Field 2B | Hopkinton B6 Academy Orange | 3 - 2 | Westborough United - B6 | |
| 4 | 3311 | 9/28/19 2:30pm | High St 9v9 #2 | North Attleboro Rockets 5/6 RA | 2 - 1 | Hopkinton B6 Academy Orange | |
| 5 | 3313 | 10/5/19 1:30pm | Fruit St. Turf Field 2A | Hopkinton B6 Academy Orange | 4 - 3 | Medway Mustangs | |
| 6 | 3318 | 11/2/19 5:30pm | King Street 9v9 | Franklin Strikers | 1 - 6 | Hopkinton B6 Academy Orange | Played on 11/2 |
| 7 | 3321 | 10/19/19 2:00pm | Fruit St. Turf Field 2B | Hopkinton B6 Academy Orange | 5 - 1 | Bellingham Hawks | |
| 8 | 3322 | 10/26/19 2:30pm | Upper Haskell 2 (9v9) | Westborough United - B6 | 3 - 1 | Hopkinton B6 Academy Orange | |
| 9 | 3325 | 11/2/19 2:00pm | Fruit St. Turf Field 2B | Hopkinton B6 Academy Orange | 4 - 3 | North Attleboro Rockets 5/6 RA | |
| 10 | 3330 | 11/9/19 2:30pm | Idylbrook 9 v9 - Duplicate DO NOT USE | Medway Mustangs | 1 - 3 | Hopkinton B6 Academy Orange | |
