| 1. Ronde | 21.07.2019 | Guadalupe | - | LD Alajuelense | 1:1 | ||||
| 2. Ronde | 25.07.2019 | Santos de Guápiles | - | Guadalupe | 0:2 | ||||
| 3. Ronde | 29.07.2019 | Guadalupe | - | Municipal Pérez Zeledón | 1:2 | ||||
| 4. Ronde | 04.08.2019 | Deportivo Saprissa | - | Guadalupe | 4:1 | ||||
| 5. Ronde | 12.08.2019 | Guadalupe | - | Limón FC | 4:3 | ||||
| 7. Ronde | 18.08.2019 | CS Herediano | - | Guadalupe | 2:0 | ||||
| 8. Ronde | 25.08.2019 | Guadalupe | - | Jicaral | 1:1 | ||||
| 14. Ronde | 22.09.2019 | Municipal Pérez Zeledón | - | Guadalupe | 0:1 | ||||
| 15. Ronde | 29.09.2019 | Guadalupe | - | Deportivo Saprissa | 2:1 | ||||
| 16. Ronde | 06.10.2019 | Limón FC | - | Guadalupe | 2:1 | ||||
| 20. Ronde | 27.10.2019 | Guadalupe | - | Municipal Grecia | 2:1 | ||||
| 21. Ronde | 03.11.2019 | CS Cartaginés | - | Guadalupe | 2:1 | ||||
| 22. Ronde | 21.11.2019 | Guadalupe | - | AD San Carlos | 2:2 |
Costa Rica