| 11. Jornada | 04.05.2019 | Santiago Wanderers | - | Deportes Melipilla | 2:1 | ||||
| 13. Jornada | 18.05.2019 | Santiago Wanderers | - | Deportes Copiapó | 0:3 | ||||
| 15. Jornada | 02.06.2019 | Puerto Montt | - | Santiago Wanderers | 2:1 | ||||
| 16. Jornada | 30.07.2019 | Deportes Melipilla | - | Santiago Wanderers | 2:1 | ||||
| 18. Jornada | 10.08.2019 | Deportes Temuco | - | Santiago Wanderers | 0:0 | ||||
| 20. Jornada | 27.08.2019 | Santiago Wanderers | - | Santa Cruz | 3:1 |
Chile