| 6. Jornada | 21.03.2023 | Santiago Wanderers | - | Unión San Felipe | 3:2 | ||||
| 7. Jornada | 27.03.2023 | Cobreloa | - | Santiago Wanderers | 2:0 | ||||
| 9. Jornada | 25.04.2023 | Universidad de Concepción | - | Santiago Wanderers | 0:2 | ||||
| 10. Jornada | 30.04.2023 | Santiago Wanderers | - | Santiago Morning | 2:0 |  |
|||
| 11. Jornada | 10.05.2023 | Santiago Wanderers | - | San Marcos | 1:1 | ||||
| 12. Jornada | 16.05.2023 | Antofagasta | - | Santiago Wanderers | 0:1 | |
|||
| 13. Jornada | 23.05.2023 | Santiago Wanderers | - | Barnechea | 1:1 | ||||
| 14. Jornada | 27.05.2023 | Deportes Temuco | - | Santiago Wanderers | 2:1 | ||||
| 15. Jornada | 04.06.2023 | Santiago Wanderers | - | Deportes Iquique | 1:1 | ||||
| 16. Jornada | 17.06.2023 | Santa Cruz | - | Santiago Wanderers | 1:2 | |
|||
| 30. Jornada | 15.10.2023 | Deportes Iquique | - | Santiago Wanderers | 3:2 | |
Chile