| 1. Round | 21/07/2019 | Guadalupe | - | LD Alajuelense | 1:1 |  |
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| 2. Round | 25/07/2019 | Limón FC | - | LD Alajuelense | 1:2 | ||||
| 3. Round | 28/07/2019 | LD Alajuelense | - | CS Herediano | 3:2 | ||||
| 4. Round | 04/08/2019 | Municipal Pérez Zeledón | - | LD Alajuelense | 1:4 | ||||
| 5. Round | 11/08/2019 | LD Alajuelense | - | Deportivo Saprissa | 1:2 | ||||
| 8. Round | 25/08/2019 | LD Alajuelense | - | Santos de Guápiles | 2:2 | ||||
| 10. Round | 05/09/2019 | LD Alajuelense | - | AD San Carlos | 1:0 | ||||
| 17. Round | 12/10/2019 | LD Alajuelense | - | Municipal Grecia | 1:0 | ||||
| 18. Round | 18/10/2019 | La U Universitarios | - | LD Alajuelense | 0:3 |
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Spain