| 2. Round | 17/01/2021 | CS Cartaginés | - | Guadalupe | 2:1 |  |
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| 3. Round | 20/01/2021 | AD San Carlos | - | Guadalupe | 1:0 | ||||
| 4. Round | 26/01/2021 | Guadalupe | - | Deportivo Saprissa | 2:2 |  |
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| 5. Round | 01/02/2021 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| 6. Round | 04/02/2021 | CS Herediano | - | Guadalupe | 2:2 | |
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| 7. Round | 06/02/2021 | Guadalupe | - | Sporting FC | 0:0 | |
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| 8. Round | 16/02/2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:3 | |
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| 9. Round | 21/02/2021 | Guadalupe | - | Municipal Grecia | 1:1 | ||||
| 11. Round | 04/03/2021 | Guadalupe | - | LD Alajuelense | 1:3 |  |
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| 17. Round | 11/04/2021 | Guadalupe | - | CS Herediano | 2:2 | ||||
| 18. Round | 18/04/2021 | Sporting FC | - | Guadalupe | 0:3 | ||||
| 19. Round | 21/04/2021 | Guadalupe | - | Municipal Pérez Zeledón | 0:1 | ||||
| 20. Round | 25/04/2021 | Municipal Grecia | - | Guadalupe | 0:0 | ||||
| 21. Round | 01/05/2021 | Guadalupe | - | Jicaral | 0:0 | |
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| 22. Round | 13/05/2021 | LD Alajuelense | - | Guadalupe | 0:0 | |
Argentina