| 1 | 6803 | 9/7/19 9:00am | Filippello Park - Grove St | Watertown REBELS | 1 - 4 | Brookline Lions | |
| 2 | 6805 | 9/14/19 9:00am | Filippello Park - Grove St | Watertown REBELS | 0 - 2 | Newton G Fury | |
| 3 | 6806 | 9/21/19 9:00am | Rotch Field 11v11 | South End Storm | 1 - 0 | Watertown REBELS | |
| 4 | 6810 | 9/28/19 4:15pm | Filippello Park - Grove St | Watertown REBELS | 1 - 2 | Brookline Lions | |
| 5 | 6813 | 10/5/19 9:00am | Filippello Park - Grove St | Watertown REBELS | 1 - 4 | Cambridge Cobras | |
| 6 | 6815 | 10/12/19 10:30am | Beaver Country Day School | Brookline Lions | 5 - 0 | Watertown REBELS | |
| 7 | 6818 | 10/19/19 1:30pm | Warren Field / McGrath Park B | Newton G Fury | 3 - 1 | Watertown REBELS | |
| 7 | 6817 | 10/20/19 8:45am | Victory Field | Watertown REBELS | 0 - 4 | Cambridge Cobras | |
| 8 | 6820 | 10/26/19 9:00am | Filippello Park - Grove St | Watertown REBELS | 0 - 2 | South End Storm | |
| 10 | 6824 | 11/9/19 9:00am | Danehy 1 - Artificial Turf | Cambridge Cobras | 1 - 1 | Watertown REBELS | |
