| 4. Round | 23/01/2020 | Guadalupe | - | AD San Carlos | 0:2 | ||||
| 5. Round | 26/01/2020 | Limón FC | - | Guadalupe | 0:0 |  |
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| 6. Round | 31/01/2020 | Guadalupe | - | CS Herediano | 0:0 | |
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| 7. Round | 06/02/2020 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 | |
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| 9. Round | 13/02/2020 | LD Alajuelense | - | Guadalupe | 3:2 | |
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| 10. Round | 16/02/2020 | Jicaral | - | Guadalupe | 0:0 | |
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| 12. Round | 01/03/2020 | La U Universitarios | - | Guadalupe | 3:0 | ||||
| 13. Round | 06/03/2020 | Guadalupe | - | Deportivo Saprissa | 2:1 | |
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| 14. Round | 08/03/2020 | Santos de Guápiles | - | Guadalupe | 3:4 |  |
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| 15. Round | 16/03/2020 | AD San Carlos | - | Guadalupe | 2:2 | |
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| 16. Round | 19/05/2020 | Guadalupe | - | Limón FC | 1:0 | ||||
| 17. Round | 25/05/2020 | CS Herediano | - | Guadalupe | 0:0 | ||||
| 18. Round | 28/05/2020 | Guadalupe | - | Municipal Pérez Zeledón | 3:1 | ||||
| 19. Round | 30/05/2020 | Municipal Grecia | - | Guadalupe | 2:0 | |
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| 20. Round | 05/06/2020 | Guadalupe | - | LD Alajuelense | 3:0 | |
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| 21. Round | 07/06/2020 | Guadalupe | - | Jicaral | 1:1 | ||||
| 22. Round | 11/06/2020 | CS Cartaginés | - | Guadalupe | 0:0 | |
Argentina