| 2. Round | 23/08/2020 | Santos de Guápiles | - | CS Herediano | 1:1 | ||||
| 3. Round | 30/08/2020 | CS Herediano | - | LD Alajuelense | 1:2 | ||||
| 4. Round | 03/09/2020 | CS Herediano | - | Municipal Pérez Zeledón | 2:1 | ||||
| 5. Round | 05/09/2020 | Guadalupe | - | CS Herediano | 2:3 | ||||
| 6. Round | 12/09/2020 | Municipal Pérez Zeledón | - | CS Herediano | 1:0 |  |
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| 7. Round | 20/09/2020 | CS Herediano | - | Guadalupe | 3:1 |  |
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| 10. Round | 24/10/2020 | Municipal Grecia | - | CS Herediano | 2:2 | ||||
| 11. Round | 28/10/2020 | CS Herediano | - | AD San Carlos | 1:1 | |
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| 12. Round | 31/10/2020 | CS Herediano | - | Sporting FC | 4:2 | ||||
| 15. Round | 17/11/2020 | CS Cartaginés | - | CS Herediano | 0:1 | ||||
| 14. Round | 22/11/2020 | CS Herediano | - | Deportivo Saprissa | 2:3 | ||||
| 13. Round | 02/12/2020 | Limón FC | - | CS Herediano | 1:4 | ||||
| 16. Round | 05/12/2020 | Jicaral | - | CS Herediano | 0:0 |
Costa Rica