| 5. Round | 15/08/2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 | ||||
| 6. Round | 18/08/2021 | Guadalupe | - | Sporting FC | 2:2 | ||||
| 10. Round | 12/09/2021 | Guadalupe | - | LD Alajuelense | 2:4 | ||||
| 11. Round | 17/09/2021 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| 12. Round | 19/09/2021 | Guadalupe | - | CS Herediano | 0:2 | ||||
| 13. Round | 26/09/2021 | AD San Carlos | - | Guadalupe | 4:2 | ||||
| 15. Round | 15/10/2021 | Deportivo Saprissa | - | Guadalupe | 4:0 | ||||
| 17. Round | 23/10/2021 | Sporting FC | - | Guadalupe | 2:0 | ||||
| 18. Round | 27/10/2021 | Guadalupe | - | CS Cartaginés | 1:1 | ||||
| 19. Round | 30/10/2021 | Guadalupe | - | Jicaral | 2:0 | ||||
| 20. Round | 21/11/2021 | Municipal Grecia | - | Guadalupe | 0:0 |
Costa Rica