| 5. Ronde | 15.08.2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 | ||||
| 6. Ronde | 18.08.2021 | Guadalupe | - | Sporting FC | 2:2 | ||||
| 10. Ronde | 12.09.2021 | Guadalupe | - | LD Alajuelense | 2:4 | ||||
| 11. Ronde | 17.09.2021 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| 12. Ronde | 19.09.2021 | Guadalupe | - | CS Herediano | 0:2 | ||||
| 13. Ronde | 26.09.2021 | AD San Carlos | - | Guadalupe | 4:2 | ||||
| 15. Ronde | 15.10.2021 | Deportivo Saprissa | - | Guadalupe | 4:0 | ||||
| 17. Ronde | 23.10.2021 | Sporting FC | - | Guadalupe | 2:0 | ||||
| 18. Ronde | 27.10.2021 | Guadalupe | - | CS Cartaginés | 1:1 | ||||
| 19. Ronde | 30.10.2021 | Guadalupe | - | Jicaral | 2:0 | ||||
| 20. Ronde | 21.11.2021 | Municipal Grecia | - | Guadalupe | 0:0 |
Costa Rica