| 3. Round | 07/08/2021 | AD San Carlos | - | Municipal Pérez Zeledón | 1:1 |  |
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| 4. Round | 12/08/2021 | CS Herediano | - | Municipal Pérez Zeledón | 1:0 | ||||
| 5. Round | 15/08/2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 |  |
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| 6. Round | 17/08/2021 | Municipal Grecia | - | Municipal Pérez Zeledón | 1:0 |  |
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| 8. Round | 29/08/2021 | Municipal Pérez Zeledón | - | Santos de Guápiles | 1:1 | ||||
| 9. Round | 08/09/2021 | CS Cartaginés | - | Municipal Pérez Zeledón | 2:1 | ||||
| 10. Round | 11/09/2021 | Sporting FC | - | Municipal Pérez Zeledón | 1:1 | |
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| 11. Round | 15/09/2021 | Municipal Pérez Zeledón | - | LD Alajuelense | 1:0 | |
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| 12. Round | 18/09/2021 | Jicaral | - | Municipal Pérez Zeledón | 3:0 | ||||
| 13. Round | 27/09/2021 | Deportivo Saprissa | - | Municipal Pérez Zeledón | 3:0 | ||||
| 14. Round | 03/10/2021 | Municipal Pérez Zeledón | - | AD San Carlos | 1:1 | |
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| 15. Round | 12/10/2021 | Municipal Pérez Zeledón | - | CS Herediano | 0:1 | |
Colombia