| 1 | 5191 | 11/2/19 4:30pm | Beaver Country Day School | Brookline Ajax | 3 - 5 | Watertown WARRIORS | |
| 2 | 5194 | 9/14/19 10:30am | Filippello Park - Grove St | Watertown WARRIORS | 4 - 1 | Framingham FC Flyers | |
| 3 | 5198 | 9/21/19 9:00am | Sprague 3 (turf) | Wellesley Chargers | 2 - 1 | Watertown WARRIORS | |
| 4 | 5200 | 9/28/19 9:00am | Filippello Park - Grove St | Watertown WARRIORS | 4 - 1 | Bedford Banshees | |
| 5 | 5205 | 10/5/19 9:00am | English High School 11v11 | JP Panthers | 0 - 2 | Watertown WARRIORS | |
| 6 | 5206 | Unscheduled | Filippello Park - Grove St | Watertown WARRIORS | 1 - F | Brookline Ajax | |
| 7 | 5210 | 10/19/19 9:00am | Warren Field / McGrath Park B | Newton G Wookies | 3 - 0 | Watertown WARRIORS | |
| 8 | 5212 | 10/26/19 10:30am | Filippello Park - Grove St | Watertown WARRIORS | 0 - 0 | Wellesley Chargers | |
| 9 | 5216 | 11/2/19 9:00am | HS Turf Field | Bedford Banshees | 1 - 0 | Watertown WARRIORS | |
| 10 | 5218 | 11/9/19 9:00am | Filippello Park - Grove St | Watertown WARRIORS | 4 - 3 | Norwood Storm | |
