| 4. Round | 23/01/2020 | Deportivo Saprissa | - | Municipal Pérez Zeledón | 0:0 | ||||
| 6. Round | 30/01/2020 | CS Cartaginés | - | Municipal Pérez Zeledón | 0:3 | ||||
| 7. Round | 06/02/2020 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 | ||||
| 9. Round | 14/02/2020 | Municipal Pérez Zeledón | - | Santos de Guápiles | 3:3 | ||||
| 10. Round | 16/02/2020 | La U Universitarios | - | Municipal Pérez Zeledón | 2:0 | ||||
| 12. Round | 01/03/2020 | Municipal Pérez Zeledón | - | Jicaral | 2:0 |  |
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| 13. Round | 05/03/2020 | LD Alajuelense | - | Municipal Pérez Zeledón | 2:0 | ||||
| 16. Round | 20/05/2020 | Municipal Grecia | - | Municipal Pérez Zeledón | 1:0 | ||||
| 17. Round | 23/05/2020 | Municipal Pérez Zeledón | - | CS Cartaginés | 0:1 | ||||
| 18. Round | 28/05/2020 | Guadalupe | - | Municipal Pérez Zeledón | 3:1 | ||||
| 19. Round | 31/05/2020 | Municipal Pérez Zeledón | - | Limón FC | 1:1 | ||||
| 20. Round | 04/06/2020 | Santos de Guápiles | - | Municipal Pérez Zeledón | 3:1 | ||||
| 21. Round | 07/06/2020 | Municipal Pérez Zeledón | - | La U Universitarios | 3:2 | |
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| 22. Round | 10/06/2020 | CS Herediano | - | Municipal Pérez Zeledón | 1:1 |
Jamaica