| 1. Round | 15/08/2020 | Guadalupe | - | Santos de Guápiles | 2:2 | ||||
| 2. Round | 23/08/2020 | LD Alajuelense | - | Guadalupe | 0:1 | ||||
| 4. Round | 02/09/2020 | Guadalupe | - | Municipal Grecia | 1:0 | ||||
| 5. Round | 05/09/2020 | Guadalupe | - | CS Herediano | 2:3 | ||||
| 6. Round | 13/09/2020 | Municipal Grecia | - | Guadalupe | 0:1 | ||||
| 8. Round | 26/09/2020 | Guadalupe | - | Municipal Pérez Zeledón | 4:1 |  |
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| 9. Round | 04/10/2020 | Guadalupe | - | LD Alajuelense | 1:2 | ||||
| 11. Round | 30/10/2020 | Guadalupe | - | CS Cartaginés | 1:0 |
Costa Rica