| 6. Round | 13/09/2020 | Municipal Grecia | - | Guadalupe | 0:1 |  |
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| 7. Round | 20/09/2020 | CS Herediano | - | Guadalupe | 3:1 | ||||
| 8. Round | 26/09/2020 | Guadalupe | - | Municipal Pérez Zeledón | 4:1 | ||||
| 9. Round | 04/10/2020 | Guadalupe | - | LD Alajuelense | 1:2 | |
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| 11. Round | 30/10/2020 | Guadalupe | - | CS Cartaginés | 1:0 | ||||
| 12. Round | 01/11/2020 | Jicaral | - | Guadalupe | 3:1 | ||||
| 10. Round | 05/11/2020 | Santos de Guápiles | - | Guadalupe | 1:1 | ||||
| 13. Round | 08/11/2020 | Guadalupe | - | Sporting FC | 2:2 | ||||
| 14. Round | 11/11/2020 | Limón FC | - | Guadalupe | 2:1 | |
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| 15. Round | 15/11/2020 | Deportivo Saprissa | - | Guadalupe | 5:1 |
Costa Rica