| 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 | ||||
| 6. Ronde | 15.08.2019 | La U Universitarios | - | Guadalupe | 2:2 | ||||
| 7. Ronde | 18.08.2019 | CS Herediano | - | Guadalupe | 2:0 | ||||
| 10. Ronde | 06.09.2019 | Guadalupe | - | CS Cartaginés | 1:0 |  |
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| 11. Ronde | 08.09.2019 | AD San Carlos | - | Guadalupe | 3:1 | ||||
| 12. Ronde | 14.09.2019 | LD Alajuelense | - | Guadalupe | 2:1 | ||||
| 13. Ronde | 19.09.2019 | Guadalupe | - | Santos de Guápiles | 2:4 | ||||
| 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 | ||||
| 17. Ronde | 11.10.2019 | Guadalupe | - | La U Universitarios | 1:0 | ||||
| 18. Ronde | 17.10.2019 | Guadalupe | - | CS Herediano | 1:1 | ||||
| 19. Ronde | 20.10.2019 | Jicaral | - | Guadalupe | 2:0 |
Costa Rica