| 1. Round | 12/01/2020 | Municipal Grecia | - | CS Herediano | 3:3 | ||||
| 2. Round | 16/01/2020 | CS Herediano | - | Jicaral | 1:0 | ||||
| 3. Round | 19/01/2020 | LD Alajuelense | - | CS Herediano | 0:0 | ||||
| 4. Round | 22/01/2020 | Limón FC | - | CS Herediano | 0:2 |  |
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| 7. Round | 06/02/2020 | CS Herediano | - | La U Universitarios | 5:2 | ||||
| 9. Round | 13/02/2020 | CS Herediano | - | CS Cartaginés | 3:0 |  |
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| 10. Round | 16/02/2020 | CS Herediano | - | AD San Carlos | 3:3 | ||||
| 12. Round | 29/02/2020 | Municipal Grecia | - | CS Herediano | 0:0 | ||||
| 13. Round | 04/03/2020 | Jicaral | - | CS Herediano | 1:1 | ||||
| 15. Round | 16/03/2020 | CS Herediano | - | Limón FC | 0:1 | |
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| 16. Round | 21/05/2020 | Deportivo Saprissa | - | CS Herediano | 1:0 | ||||
| 19. Round | 31/05/2020 | CS Herediano | - | Santos de Guápiles | 3:1 | |
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| 20. Round | 04/06/2020 | CS Cartaginés | - | CS Herediano | 1:4 | ||||
| 21. Round | 08/06/2020 | AD San Carlos | - | CS Herediano | 1:3 | ||||
| 22. Round | 10/06/2020 | CS Herediano | - | Municipal Pérez Zeledón | 1:1 |
Costa Rica