| 8. Round | 10/09/2023 | CS Cartaginés | - | CS Herediano | 1:1 | ||||
| 9. Round | 14/09/2023 | CS Herediano | - | AD San Carlos | 2:1 | ||||
| 11. Round | 21/09/2023 | Sporting FC | - | CS Herediano | 1:3 |  |
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| 12. Round | 24/09/2023 | CS Herediano | - | Municipal Liberia | 2:2 | ||||
| 13. Round | 01/10/2023 | Municipal Pérez Zeledón | - | CS Herediano | 1:4 | ||||
| 14. Round | 08/10/2023 | CS Herediano | - | Deportivo Saprissa | 2:0 | ||||
| 16. Round | 22/10/2023 | CS Herediano | - | Puntarenas FC | 2:1 | ||||
| 18. Round | 05/11/2023 | Municipal Grecia | - | CS Herediano | 0:0 | ||||
| 19. Round | 09/11/2023 | CS Herediano | - | CS Cartaginés | 1:0 | |
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| 20. Round | 12/11/2023 | AD San Carlos | - | CS Herediano | 2:1 |  |
Costa Rica