| 1 | 1901 | 4/25/24 6:30pm | Victory Oval Field 1 (7v7) | Watertown Jackrabbits | 2 - 2 | Watertown Jackabees | Rescheduled to 04/25/24 |
| 2 | 1904 | 4/13/24 10:15am | Victory Oval Field 2 (7v7) | Watertown Jackabees | 2 - 4 | Brookline Barcelona | |
| 3 | 1908 | 4/28/24 12:00pm | Leonard 7v7-1 | Winchester Spirit | 1 - 4 | Watertown Jackabees | |
| 4 | 1910 | 4/27/24 9:00am | Victory Oval Field 2 (7v7) | Watertown Jackabees | 0 - 4 | Winchester Courage | |
| 5 | 1915 | 5/4/24 9:00am | MathWorks Upper (7v7) | Natick Lightning Dogs | 2 - 6 | Watertown Jackabees | |
| 6 | 1916 | 5/11/24 8:00am | Victory Oval Field 2 (7v7) | Watertown Jackabees | 2 - 2 | Watertown Jackrabbits | |
| 7 | 1920 | 5/18/24 9:00am | Soule Recreation Center | Brookline Barcelona | 2 - 0 | Watertown Jackabees | |
| 8 | 1922 | 5/25/24 9:00am | Victory Oval Field 2 (7v7) | Watertown Jackabees | 2 - 0 | Newton G United FC | |
| 9 | 1926 | 6/1/24 10:30am | Skillings Grass 7v7-2 | Winchester Courage | 2 - 1 | Watertown Jackabees | |
| 10 | 1928 | 6/8/24 9:00am | Victory Oval Field 2 (7v7) | Watertown Jackabees | 2 - 0 | Natick Lightning Dogs | |
