| 2. Ronde | 17.01.2021 | CS Cartaginés | - | Guadalupe | 2:1 |  |
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| 3. Ronde | 21.01.2021 | AD San Carlos | - | Guadalupe | 1:0 | ||||
| 4. Ronde | 26.01.2021 | Guadalupe | - | Deportivo Saprissa | 2:2 |  |
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| 5. Ronde | 01.02.2021 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| 6. Ronde | 04.02.2021 | CS Herediano | - | Guadalupe | 2:2 | |
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| 7. Ronde | 06.02.2021 | Guadalupe | - | Sporting FC | 0:0 | |
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| 8. Ronde | 16.02.2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:3 | |
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| 9. Ronde | 21.02.2021 | Guadalupe | - | Municipal Grecia | 1:1 | ||||
| 11. Ronde | 04.03.2021 | Guadalupe | - | LD Alajuelense | 1:3 |  |
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| 17. Ronde | 11.04.2021 | Guadalupe | - | CS Herediano | 2:2 | ||||
| 18. Ronde | 18.04.2021 | Sporting FC | - | Guadalupe | 0:3 | ||||
| 19. Ronde | 22.04.2021 | Guadalupe | - | Municipal Pérez Zeledón | 0:1 | ||||
| 20. Ronde | 25.04.2021 | Municipal Grecia | - | Guadalupe | 0:0 | ||||
| 21. Ronde | 02.05.2021 | Guadalupe | - | Jicaral | 0:0 | |
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| 22. Ronde | 13.05.2021 | LD Alajuelense | - | Guadalupe | 0:0 | |
Argentinië