| 1 | 3333 | 9/7/24 12:00pm | Lincoln Fields2 | Lexington Lightning | 1 - 3 | Watertown Jackabees | |
| 2 | 3336 | 9/14/24 10:30am | Victory Oval | Watertown Jackabees | 4 - 0 | Southboro Courage | |
| 3 | 3339 | 9/21/24 10:30am | Victory Oval | Watertown Jackabees | 5 - 0 | Westborough United - G5 | |
| 4 | 3342 | 9/28/24 11:45am | Beaver Pond/Chilson Beach | Franklin Strikers | 0 - 4 | Watertown Jackabees | |
| 5 | 3254 | 10/5/24 10:30am | Victory Oval | Watertown Jackabees | 0 - 0 | Brookline Barcelona | |
| 6 | 3257 | 10/22/24 7:00pm | Filippello Park - Grove St | Watertown Jackabees | 1 - 2 | Newton G United FC | |
| 7 | 3261 | 11/2/24 2:30pm | Thurston Upper 9v9 | Westwood Cosmic Crushers | 2 - 2 | Watertown Jackabees | |
| 8 | 3264 | 10/26/24 9:00am | Filippello Park - Grove St | Watertown Jackabees | 2 - 3 | Parkway United Royal | |
| 9 | 3266 | 11/2/24 10:30am | Victory Oval | Watertown Jackabees | 3 - 0 | Dedham Maroon Devils | |
| 10 | 3269 | 11/9/24 10:30am | Skyline Park | Brookline Barcelona | 3 - 2 | Watertown Jackabees | |
