| 4. Round | 23/01/2020 | Guadalupe | - | AD San Carlos | 0:2 |  |
|||
| 9. Round | 13/02/2020 | LD Alajuelense | - | Guadalupe | 3:2 | ||||
| 14. Round | 08/03/2020 | Santos de Guápiles | - | Guadalupe | 3:4 | ||||
| 15. Round | 16/03/2020 | AD San Carlos | - | Guadalupe | 2:2 | ||||
| 18. Round | 28/05/2020 | Guadalupe | - | Municipal Pérez Zeledón | 3:1 | ||||
| 22. Round | 11/06/2020 | CS Cartaginés | - | Guadalupe | 0:0 |
Costa Rica