| 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 | ||||
| 9. Ronde | 01.09.2019 | Municipal Grecia | - | Guadalupe | 2:1 | ||||
| 10. Ronde | 06.09.2019 | Guadalupe | - | CS Cartaginés | 1:0 | ||||
| 20. Ronde | 27.10.2019 | Guadalupe | - | Municipal Grecia | 2:1 |  |
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| 21. Ronde | 03.11.2019 | CS Cartaginés | - | Guadalupe | 2:1 | |
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| 22. Ronde | 21.11.2019 | Guadalupe | - | AD San Carlos | 2:2 | |
Costa Rica