| 1 | 3181 | 9/7/19 4:30pm | Downes Field (oval) | Brookline Inter | 4 - 2 | Belmont B6-2 Condors | |
| 2 | 3184 | 9/14/19 2:30pm | Belmont Day School - Clafin Field | Belmont B6-2 Condors | 4 - 3 | Cambridge Revs | |
| 3 | 3188 | 9/21/19 2:30pm | Devoll 9v9 Field | Canton United | 2 - 3 | Belmont B6-2 Condors | |
| 4 | 3190 | 9/28/19 2:30pm | Belmont Day School - Clafin Field | Belmont B6-2 Condors | 9 - 2 | Milton Atletico | |
| 5 | 3195 | 10/5/19 2:30pm | Pagel Field | JP Atlético | 3 - 1 | Belmont B6-2 Condors | |
| 6 | 3196 | 10/12/19 2:30pm | Grove St. (4B) | Belmont B6-2 Condors | 3 - 2 | Brookline Inter | |
| 7 | 3200 | 10/19/19 2:00pm | Danehy 2 - artificial turf | Cambridge Revs | 3 - 0 | Belmont B6-2 Condors | |
| 8 | 3202 | 10/26/19 2:30pm | Grove St. (4A) | Belmont B6-2 Condors | 4 - 1 | Canton United | |
| 9 | 3206 | 11/2/19 2:30pm | Kelly Field | Milton Atletico | 0 - 3 | Belmont B6-2 Condors | |
| 10 | 3208 | 11/9/19 2:30pm | Belmont Day School - Far Field | Belmont B6-2 Condors | 0 - 2 | JP Atlético | |
