| 1. Round | 21/07/2019 | Guadalupe | - | LD Alajuelense | 1:1 | ||||
| 2. Round | 25/07/2019 | Santos de Guápiles | - | Guadalupe | 0:2 | ||||
| 3. Round | 29/07/2019 | Guadalupe | - | Municipal Pérez Zeledón | 1:2 | ||||
| 4. Round | 04/08/2019 | Deportivo Saprissa | - | Guadalupe | 4:1 | ||||
| 5. Round | 12/08/2019 | Guadalupe | - | Limón FC | 4:3 | ||||
| 6. Round | 15/08/2019 | La U Universitarios | - | Guadalupe | 2:2 |  |
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| 7. Round | 18/08/2019 | CS Herediano | - | Guadalupe | 2:0 |
Costa Rica