| 1. Round | 21/07/2019 | La U Universitarios | - | CS Herediano | 0:1 | ||||
| 2. Round | 25/07/2019 | CS Herediano | - | Municipal Grecia | 3:0 | ||||
| 3. Round | 28/07/2019 | LD Alajuelense | - | CS Herediano | 3:2 | ||||
| 4. Round | 04/08/2019 | CS Herediano | - | Jicaral | 1:2 | ||||
| 5. Round | 11/08/2019 | CS Cartaginés | - | CS Herediano | 1:1 |  |
|||
| 6. Round | 15/08/2019 | CS Herediano | - | Limón FC | 3:2 | ||||
| 10. Round | 05/09/2019 | Santos de Guápiles | - | CS Herediano | 1:1 | ||||
| 11. Round | 08/09/2019 | CS Herediano | - | Municipal Pérez Zeledón | 4:1 | ||||
| 12. Round | 11/09/2019 | CS Herediano | - | La U Universitarios | 0:0 | ||||
| 8. Round | 16/09/2019 | AD San Carlos | - | CS Herediano | 1:0 |  |
|||
| 22. Round | 16/11/2019 | Municipal Pérez Zeledón | - | CS Herediano | 1:0 |
Costa Rica