| 2. Round | 25/07/2019 | CS Herediano | - | Municipal Grecia | 3:0 | ||||
| 12. Round | 11/09/2019 | CS Herediano | - | La U Universitarios | 0:0 | ||||
| 8. Round | 16/09/2019 | AD San Carlos | - | CS Herediano | 1:0 |  |
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| 13. Round | 18/09/2019 | Municipal Grecia | - | CS Herediano | 2:2 |  |
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| 14. Round | 23/09/2019 | CS Herediano | - | LD Alajuelense | 0:1 | ||||
| 16. Round | 07/10/2019 | CS Herediano | - | CS Cartaginés | 3:0 | ||||
| 17. Round | 09/10/2019 | Limón FC | - | CS Herediano | 1:0 | ||||
| 9. Round | 13/10/2019 | CS Herediano | - | Deportivo Saprissa | 4:0 | |
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| 18. Round | 17/10/2019 | Guadalupe | - | CS Herediano | 1:1 | ||||
| 19. Round | 20/10/2019 | CS Herediano | - | AD San Carlos | 3:1 | |
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| 20. Round | 27/10/2019 | Deportivo Saprissa | - | CS Herediano | 2:1 | ||||
| 22. Round | 16/11/2019 | Municipal Pérez Zeledón | - | CS Herediano | 1:0 | |
Costa Rica