| 6. Round | 28/08/2023 | CS Herediano | - | LD Alajuelense | 2:3 | ||||
| 7. Round | 03/09/2023 | CS Herediano | - | Municipal Grecia | 3:0 | ||||
| 8. Round | 10/09/2023 | CS Cartaginés | - | CS Herediano | 1:1 | ||||
| 9. Round | 14/09/2023 | CS Herediano | - | AD San Carlos | 2:1 | ||||
| 10. Round | 17/09/2023 | Santos de Guápiles | - | CS Herediano | 1:1 | ||||
| 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 | ||||
| 15. Round | 15/11/2023 | AD Guanacasteca | - | CS Herediano | 0:1 | ||||
| 21. Round | 23/11/2023 | CS Herediano | - | Santos de Guápiles | 3:0 | ||||
| 22. Round | 26/11/2023 | CS Herediano | - | Sporting FC | 3:0 |  |
Costa Rica