| 3. Jornada | 30.08.2020 | Municipal Pérez Zeledón | - | Guadalupe | 3:2 | ||||
| 4. Jornada | 02.09.2020 | Guadalupe | - | Municipal Grecia | 1:0 | ||||
| 5. Jornada | 05.09.2020 | Guadalupe | - | CS Herediano | 2:3 | ||||
| 12. Jornada | 01.11.2020 | Jicaral | - | Guadalupe | 3:1 | ||||
| 10. Jornada | 06.11.2020 | Santos de Guápiles | - | Guadalupe | 1:1 | ||||
| 15. Jornada | 15.11.2020 | Deportivo Saprissa | - | Guadalupe | 5:1 | ||||
| 16. Jornada | 06.12.2020 | Guadalupe | - | AD San Carlos | 3:0 |
Costa Rica