| 2. Jornada | 17.01.2021 | CS Cartaginés | - | Guadalupe | 2:1 | ||||
| 4. Jornada | 26.01.2021 | Guadalupe | - | Deportivo Saprissa | 2:2 | ||||
| 5. Jornada | 01.02.2021 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| 6. Jornada | 04.02.2021 | CS Herediano | - | Guadalupe | 2:2 | ||||
| 7. Jornada | 06.02.2021 | Guadalupe | - | Sporting FC | 0:0 | ||||
| 8. Jornada | 16.02.2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:3 | ||||
| 9. Jornada | 21.02.2021 | Guadalupe | - | Municipal Grecia | 1:1 | ||||
| 10. Jornada | 27.02.2021 | Jicaral | - | Guadalupe | 3:2 |  |
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| 11. Jornada | 04.03.2021 | Guadalupe | - | LD Alajuelense | 1:3 | ||||
| 12. Jornada | 06.03.2021 | Limón FC | - | Guadalupe | 1:7 | ||||
| 13. Jornada | 14.03.2021 | Guadalupe | - | CS Cartaginés | 0:3 | |
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| 16. Jornada | 04.04.2021 | Guadalupe | - | Santos de Guápiles | 2:4 | |
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| 17. Jornada | 11.04.2021 | Guadalupe | - | CS Herediano | 2:2 | |
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| 19. Jornada | 22.04.2021 | Guadalupe | - | Municipal Pérez Zeledón | 0:1 | ||||
| 20. Jornada | 25.04.2021 | Municipal Grecia | - | Guadalupe | 0:0 | ||||
| 21. Jornada | 02.05.2021 | Guadalupe | - | Jicaral | 0:0 | ||||
| 22. Jornada | 13.05.2021 | LD Alajuelense | - | Guadalupe | 0:0 |
Costa Rica