| 1 | 2506 | 9/9/23 2:30pm | HYSA Park M-2 | Holliston B5 - Aldredge/Looney | 1 - 2 | Wellesley Honey Badgers | |
| 2 | 2511 | 9/16/23 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 3 - 3 | Holliston B5 - Aldredge/Looney | |
| 3 | 2512 | 9/23/23 12:45pm | Beaver Pond/Chilson Beach | Franklin Panthers | 3 - 1 | Holliston B5 - Aldredge/Looney | |
| 4 | 2516 | 9/30/23 2:30pm | HYSA Park M-2 | Holliston B5 - Aldredge/Looney | 3 - 2 | Newton B Flamengo | |
| 5 | 2519 | 10/10/23 6:45pm | Gonzalez Field | Dedham United | 5 - 1 | Holliston B5 - Aldredge/Looney | |
| 6 | 2521 | 10/14/23 10:30am | Sprague 3B | Wellesley Honey Badgers | 6 - 1 | Holliston B5 - Aldredge/Looney | |
| 7 | 2524 | 10/21/23 2:30pm | HYSA Park M-2 | Holliston B5 - Aldredge/Looney | 0 - 4 | Canton Boys Grade 5 United | |
| 8 | 2528 | 10/28/23 2:30pm | Weston Pond W-5 | Holliston B5 - Aldredge/Looney | 3 - 6 | Franklin Panthers | |
| 9 | 2530 | 11/4/23 2:30pm | Weeks A | Newton B Flamengo | 4 - 2 | Holliston B5 - Aldredge/Looney | |
| 10 | 2534 | 11/11/23 2:30pm | HYSA Park M-2 | Holliston B5 - Aldredge/Looney | 2 - 5 | Dedham United | |
