| 1. Round | 21/07/2019 | Guadalupe | - | LD Alajuelense | 1:1 | ||||
| 3. Round | 29/07/2019 | Guadalupe | - | Municipal Pérez Zeledón | 1:2 | ||||
| 8. Round | 25/08/2019 | Guadalupe | - | Jicaral | 1:1 | ||||
| 9. Round | 01/09/2019 | Municipal Grecia | - | Guadalupe | 2:1 | ||||
| 10. Round | 06/09/2019 | Guadalupe | - | CS Cartaginés | 1:0 | ||||
| 11. Round | 08/09/2019 | AD San Carlos | - | Guadalupe | 3:1 | ||||
| 12. Round | 14/09/2019 | LD Alajuelense | - | Guadalupe | 2:1 | ||||
| 16. Round | 06/10/2019 | Limón FC | - | Guadalupe | 2:1 |  |
Costa Rica