| 1. Round | 11/01/2020 | Guadalupe | - | La U Universitarios | 5:0 | ||||
| 2. Round | 17/01/2020 | Deportivo Saprissa | - | Guadalupe | 3:0 |  |
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| 5. Round | 26/01/2020 | Limón FC | - | Guadalupe | 0:0 | ||||
| 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 | ||||
| 3. Round | 20/02/2020 | Guadalupe | - | Santos de Guápiles | 1:0 |  |
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| 11. Round | 22/02/2020 | Guadalupe | - | CS Cartaginés | 0:0 | |
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| 13. Round | 06/03/2020 | Guadalupe | - | Deportivo Saprissa | 2:1 | ||||
| 15. Round | 16/03/2020 | AD San Carlos | - | Guadalupe | 2:2 | ||||
| 16. Round | 19/05/2020 | Guadalupe | - | Limón FC | 1:0 |
Costa Rica