| 19. Round | 23/07/2023 | Santiago Morning | - | Antofagasta | 1:2 | ||||
| 20. Round | 29/07/2023 | Unión San Felipe | - | Santiago Morning | 2:1 | ||||
| 24. Round | 27/08/2023 | Santiago Morning | - | Deportes Iquique | 0:3 | ||||
| 25. Round | 01/09/2023 | Santiago Morning | - | Santiago Wanderers | 0:0 | ||||
| 26. Round | 08/09/2023 | Santiago Morning | - | Puerto Montt | 2:2 | ||||
| 27. Round | 22/09/2023 | Rangers | - | Santiago Morning | 0:2 |  |
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| 28. Round | 01/10/2023 | Santiago Morning | - | Universidad de Concepción | 3:1 | ||||
| 29. Round | 08/10/2023 | La Serena | - | Santiago Morning | 0:1 | ||||
| 30. Round | 14/10/2023 | Santiago Morning | - | Recoleta | 0:1 |
Chile