| 7. Jornada | 20.09.2020 | CS Herediano | - | Guadalupe | 3:1 |  |
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| 8. Jornada | 27.09.2020 | Guadalupe | - | Municipal Pérez Zeledón | 4:1 | |
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| 9. Jornada | 04.10.2020 | Guadalupe | - | LD Alajuelense | 1:2 |  |
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| 11. Jornada | 30.10.2020 | Guadalupe | - | CS Cartaginés | 1:0 | ||||
| 12. Jornada | 01.11.2020 | Jicaral | - | Guadalupe | 3:1 | ||||
| 10. Jornada | 06.11.2020 | Santos de Guápiles | - | Guadalupe | 1:1 | ||||
| 13. Jornada | 09.11.2020 | Guadalupe | - | Sporting FC | 2:2 | |
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| 14. Jornada | 11.11.2020 | Limón FC | - | Guadalupe | 2:1 | |
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| 15. Jornada | 15.11.2020 | Deportivo Saprissa | - | Guadalupe | 5:1 | ||||
| 16. Jornada | 06.12.2020 | Guadalupe | - | AD San Carlos | 3:0 | |
Costa Rica