| 1. Jornada | 21.07.2019 | Guadalupe | - | LD Alajuelense | 1:1 | ||||
| 3. Jornada | 29.07.2019 | Guadalupe | - | Municipal Pérez Zeledón | 1:2 | ||||
| 8. Jornada | 25.08.2019 | Guadalupe | - | Jicaral | 1:1 | ||||
| 9. Jornada | 01.09.2019 | Municipal Grecia | - | Guadalupe | 2:1 | ||||
| 10. Jornada | 06.09.2019 | Guadalupe | - | CS Cartaginés | 1:0 | ||||
| 11. Jornada | 08.09.2019 | AD San Carlos | - | Guadalupe | 3:1 | ||||
| 12. Jornada | 14.09.2019 | LD Alajuelense | - | Guadalupe | 2:1 | ||||
| 16. Jornada | 06.10.2019 | Limón FC | - | Guadalupe | 2:1 |  |
Costa Rica