2. Round | 17/01/2021 | CS Cartaginés | - | Guadalupe | 2:1 | ||||
14. Round | 20/03/2021 | Guadalupe | - | AD San Carlos | 1:2 | ||||
15. Round | 01/04/2021 | Deportivo Saprissa | - | Guadalupe | 1:1 | ||||
16. Round | 04/04/2021 | Guadalupe | - | Santos de Guápiles | 2:4 | ||||
17. Round | 11/04/2021 | Guadalupe | - | CS Herediano | 2:2 | ||||
18. Round | 18/04/2021 | Sporting FC | - | Guadalupe | 0:3 | ||||
19. Round | 21/04/2021 | Guadalupe | - | Municipal Pérez Zeledón | 0:1 | ||||
20. Round | 25/04/2021 | Municipal Grecia | - | Guadalupe | 0:0 | ||||
21. Round | 01/05/2021 | Guadalupe | - | Jicaral | 0:0 | ||||
22. Round | 13/05/2021 | LD Alajuelense | - | Guadalupe | 0:0 |