| 1. Jornada | 17.02.2019 | Santiago Wanderers | - | Rangers | 0:0 | ||||
| 3. Jornada | 02.03.2019 | Santiago Wanderers | - | Deportes Temuco | 1:0 | ||||
| 5. Jornada | 16.03.2019 | San Luis | - | Santiago Wanderers | 2:2 | ||||
| 6. Jornada | 31.03.2019 | Santiago Wanderers | - | Deportes Valdivia | 2:0 | ||||
| 10. Jornada | 28.04.2019 | Cobreloa | - | Santiago Wanderers | 4:1 | ||||
| 11. Jornada | 04.05.2019 | Santiago Wanderers | - | Deportes Melipilla | 2:1 | ||||
| 12. Jornada | 11.05.2019 | La Serena | - | Santiago Wanderers | 0:0 | ||||
| 15. Jornada | 02.06.2019 | Puerto Montt | - | Santiago Wanderers | 2:1 | ||||
| 21. Jornada | 01.09.2019 | Deportes Valdivia | - | Santiago Wanderers | 0:1 | ||||
| 22. Jornada | 09.09.2019 | Santiago Morning | - | Santiago Wanderers | 2:1 | ||||
| 24. Jornada | 01.10.2019 | Santiago Wanderers | - | Barnechea | 0:0 | ||||
| 27. Jornada | 19.10.2019 | Rangers | - | Santiago Wanderers | 0:1 |
Brasil