| 2. Jornada | 19.02.2023 | La Serena | - | Santiago Wanderers | 3:1 |  |
|||
| 3. Jornada | 26.02.2023 | Santiago Wanderers | - | Puerto Montt | 3:1 | ||||
| 4. Jornada | 04.03.2023 | Santiago Wanderers | - | Recoleta | 1:1 | |
|||
| 5. Jornada | 15.03.2023 | San Luis | - | Santiago Wanderers | 2:0 | ||||
| 6. Jornada | 21.03.2023 | Santiago Wanderers | - | Unión San Felipe | 3:2 | |
|||
| 8. Jornada | 17.04.2023 | Santiago Wanderers | - | Rangers | 0:1 | |
|||
| 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 | ||||
| 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 | ||||
| 26. Jornada | 11.09.2023 | San Marcos | - | Santiago Wanderers | 1:2 |  |
|||
| 27. Jornada | 24.09.2023 | Santiago Wanderers | - | Antofagasta | 3:0 | |
|||
| 23. Jornada | 27.09.2023 | Rangers | - | Santiago Wanderers | 0:0 | |
Chile