| 3. Jornada | 30.08.2020 | Municipal Pérez Zeledón | - | Guadalupe | 3:2 | ||||
| 7. Jornada | 20.09.2020 | CS Herediano | - | Guadalupe | 3:1 | ||||
| 8. Jornada | 27.09.2020 | Guadalupe | - | Municipal Pérez Zeledón | 4:1 | ||||
| 12. Jornada | 01.11.2020 | Jicaral | - | Guadalupe | 3:1 | ||||
| 13. Jornada | 09.11.2020 | Guadalupe | - | Sporting FC | 2:2 | ||||
| 14. Jornada | 11.11.2020 | Limón FC | - | Guadalupe | 2:1 | ||||
| 16. Jornada | 06.12.2020 | Guadalupe | - | AD San Carlos | 3:0 |
Costa Rica