| 1 | 2253 | 4/6/19 12:00pm | DeFazio #3 Conroy | Needham Chargers | 3 - 0 | Winchester Flash | |
| 2 | 2256 | 4/26/19 5:20pm | Ryan Connolly Field 9v9-Front | Winchester Flash | 5 - 2 | Arlington Eagles | |
| 3 | 2259 | 6/8/19 3:00pm | Leonard 9v9-2 | Winchester Flash | 0 - 4 | Westwood Fisher Cats | |
| 4 | 2262 | 5/16/19 6:00pm | Weeks F | Newton G Force United | 4 - 0 | Winchester Flash | |
| 5 | 2265 | 5/4/19 9:00am | Leonard 9v9-2 | Winchester Flash | 0 - 4 | Belmont G5-1 Bald Eagles | |
| 6 | 2268 | 5/11/19 9:00am | Leonard 9v9-2 | Winchester Flash | 0 - 2 | Needham Chargers | |
| 7 | 2269 | 5/18/19 10:30am | McClennen Park 1 | Arlington Eagles | 2 - 3 | Winchester Flash | |
| 8 | 2274 | 6/1/19 10:30am | Multi-Purpose 9v9 Turf WHS | Westwood Fisher Cats | 6 - 0 | Winchester Flash | |
| 9 | 2277 | 6/8/19 9:00am | Leonard 9v9-2 | Winchester Flash | 2 - 1 | Newton G Force United | |
| 10 | 2278 | 6/15/19 9:00am | Grove St. (1A) | Belmont G5-1 Bald Eagles | 3 - 0 | Winchester Flash | |
