| 2. Round | 23/08/2020 | LD Alajuelense | - | Guadalupe | 0:1 | ||||
| 3. Round | 29/08/2020 | Municipal Pérez Zeledón | - | Guadalupe | 3:2 | ||||
| 5. Round | 05/09/2020 | Guadalupe | - | CS Herediano | 2:3 | ||||
| 6. Round | 13/09/2020 | Municipal Grecia | - | Guadalupe | 0:1 | ||||
| 7. Round | 20/09/2020 | CS Herediano | - | Guadalupe | 3:1 | ||||
| 9. Round | 04/10/2020 | Guadalupe | - | LD Alajuelense | 1:2 |  |
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| 13. Round | 08/11/2020 | Guadalupe | - | Sporting FC | 2:2 | ||||
| 15. Round | 15/11/2020 | Deportivo Saprissa | - | Guadalupe | 5:1 | ||||
| 16. Round | 06/12/2020 | Guadalupe | - | AD San Carlos | 3:0 |
Costa Rica