| 1 | 3183 | 4/6/19 10:30am | Ellsworth-McAfee Field A | Northborough Nitro | 3 - 1 | Winchester Firecats | |
| 2 | 3186 | 4/26/19 5:20pm | Ryan Connolly Field 9v9-Back | Winchester Firecats | 2 - 0 | Cambridge Breakers FC | |
| 3 | 3189 | 4/20/19 9:00am | Ryan Connolly Field 9v9-Front | Winchester Firecats | 3 - 0 | Wayland Lightning | |
| 4 | 3192 | 4/27/19 10:15am | Lower Fields 1A | A-B Thunder | 3 - 0 | Winchester Firecats | |
| 5 | 3195 | 5/4/19 9:00am | Leonard 9v9-3 | Winchester Firecats | 0 - 1 | Sudbury Academy United | |
| 6 | 3198 | 5/11/19 9:00am | Leonard 9v9-3 | Winchester Firecats | 3 - 1 | Northborough Nitro | |
| 7 | 3199 | 5/18/19 12:30pm | Danehy 1 - Artificial Turf | Cambridge Breakers FC | 4 - 1 | Winchester Firecats | |
| 8 | 3204 | 6/1/19 10:30am | Alpine Field #2 | Wayland Lightning | 1 - 0 | Winchester Firecats | |
| 9 | 3207 | 6/14/19 5:20pm | Leonard 9v9-3 | Winchester Firecats | 0 - 2 | A-B Thunder | |
| 10 | 3208 | 6/15/19 10:30am | Cutting | Sudbury Academy United | 0 - 0 | Winchester Firecats | |
