| 5. Round | 14/03/2023 | Santiago Morning | - | Unión San Felipe | 2:1 | ||||
| 6. Round | 21/03/2023 | Santiago Wanderers | - | Unión San Felipe | 3:2 | ||||
| 7. Round | 26/03/2023 | Deportes Iquique | - | Unión San Felipe | 1:2 |  |
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| 8. Round | 16/04/2023 | Unión San Felipe | - | Deportes Temuco | 1:1 | ||||
| 9. Round | 22/04/2023 | Rangers | - | Unión San Felipe | 1:3 | ||||
| 18. Round | 16/07/2023 | Antofagasta | - | Unión San Felipe | 1:2 | |
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| 19. Round | 22/07/2023 | Unión San Felipe | - | San Marcos | 3:0 | ||||
| 20. Round | 29/07/2023 | Unión San Felipe | - | Santiago Morning | 2:1 | ||||
| 21. Round | 05/08/2023 | Unión San Felipe | - | Santiago Wanderers | 0:1 | ||||
| 23. Round | 20/08/2023 | Deportes Temuco | - | Unión San Felipe | 2:1 | ||||
| 24. Round | 26/08/2023 | Unión San Felipe | - | Rangers | 4:1 | ||||
| 25. Round | 05/09/2023 | La Serena | - | Unión San Felipe | 2:0 | ||||
| 26. Round | 10/09/2023 | Unión San Felipe | - | Santa Cruz | 0:0 | ||||
| 27. Round | 24/09/2023 | Cobreloa | - | Unión San Felipe | 1:0 | |
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| 28. Round | 30/09/2023 | Unión San Felipe | - | Recoleta | 1:2 | ||||
| 29. Round | 08/10/2023 | Universidad de Concepción | - | Unión San Felipe | 0:0 | ||||
| 30. Round | 14/10/2023 | Unión San Felipe | - | Puerto Montt | 0:1 |
Chile