| 6. Round | 15/08/2019 | La U Universitarios | - | Guadalupe | 2:2 | ||||
| 14. Round | 22/09/2019 | Municipal Pérez Zeledón | - | Guadalupe | 0:1 | ||||
| 15. Round | 28/09/2019 | Guadalupe | - | Deportivo Saprissa | 2:1 | ||||
| 16. Round | 06/10/2019 | Limón FC | - | Guadalupe | 2:1 | ||||
| 17. Round | 11/10/2019 | Guadalupe | - | La U Universitarios | 1:0 |  |
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| 18. Round | 17/10/2019 | Guadalupe | - | CS Herediano | 1:1 |
Costa Rica