| 6. Jornada | 13.09.2020 | Municipal Grecia | - | Guadalupe | 0:1 | ||||
| 8. Jornada | 27.09.2020 | Guadalupe | - | Municipal Pérez Zeledón | 4:1 | ||||
| 9. Jornada | 04.10.2020 | Guadalupe | - | LD Alajuelense | 1:2 | ||||
| 11. Jornada | 30.10.2020 | Guadalupe | - | CS Cartaginés | 1:0 | ||||
| 12. Jornada | 01.11.2020 | Jicaral | - | Guadalupe | 3:1 | ||||
| 10. Jornada | 06.11.2020 | Santos de Guápiles | - | Guadalupe | 1:1 | ||||
| 13. Jornada | 09.11.2020 | Guadalupe | - | Sporting FC | 2:2 | ||||
| 16. Jornada | 06.12.2020 | Guadalupe | - | AD San Carlos | 3:0 |
Costa Rica