| 3. Jornada | 28.07.2019 | LD Alajuelense | - | CS Herediano | 3:2 |  |
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| 7. Jornada | 18.08.2019 | CS Herediano | - | Guadalupe | 2:0 | ||||
| 10. Jornada | 05.09.2019 | Santos de Guápiles | - | CS Herediano | 1:1 | ||||
| 11. Jornada | 08.09.2019 | CS Herediano | - | Municipal Pérez Zeledón | 4:1 | ||||
| 12. Jornada | 11.09.2019 | CS Herediano | - | La U Universitarios | 0:0 |  |
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| 8. Jornada | 16.09.2019 | AD San Carlos | - | CS Herediano | 1:0 | |
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| 13. Jornada | 18.09.2019 | Municipal Grecia | - | CS Herediano | 2:2 | ||||
| 14. Jornada | 23.09.2019 | CS Herediano | - | LD Alajuelense | 0:1 | ||||
| 17. Jornada | 09.10.2019 | Limón FC | - | CS Herediano | 1:0 | ||||
| 9. Jornada | 13.10.2019 | CS Herediano | - | Deportivo Saprissa | 4:0 | ||||
| 22. Jornada | 17.11.2019 | Municipal Pérez Zeledón | - | CS Herediano | 1:0 |
Costa Rica
Nicaragua