| 3. Round | 26/02/2023 | Santiago Wanderers | - | Puerto Montt | 3:1 | ||||
| 4. Round | 04/03/2023 | Santiago Wanderers | - | Recoleta | 1:1 |  |
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| 5. Round | 14/03/2023 | San Luis | - | Santiago Wanderers | 2:0 | ||||
| 11. Round | 10/05/2023 | Santiago Wanderers | - | San Marcos | 1:1 | ||||
| 12. Round | 16/05/2023 | Antofagasta | - | Santiago Wanderers | 0:1 | ||||
| 13. Round | 22/05/2023 | Santiago Wanderers | - | Barnechea | 1:1 | ||||
| 15. Round | 04/06/2023 | Santiago Wanderers | - | Deportes Iquique | 1:1 | ||||
| 25. Round | 01/09/2023 | Santiago Morning | - | Santiago Wanderers | 0:0 | ||||
| 26. Round | 11/09/2023 | San Marcos | - | Santiago Wanderers | 1:2 | ||||
| 27. Round | 24/09/2023 | Santiago Wanderers | - | Antofagasta | 3:0 | ||||
| 23. Round | 27/09/2023 | Rangers | - | Santiago Wanderers | 0:0 | |
Chile