| 3. Round | 28/07/2019 | LD Alajuelense | - | CS Herediano | 3:2 | ||||
| 5. Round | 11/08/2019 | CS Cartaginés | - | CS Herediano | 1:1 | ||||
| 6. Round | 15/08/2019 | CS Herediano | - | Limón FC | 3:2 | ||||
| 7. Round | 18/08/2019 | CS Herediano | - | Guadalupe | 2:0 |  |
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| 10. Round | 05/09/2019 | Santos de Guápiles | - | CS Herediano | 1:1 | ||||
| 11. Round | 08/09/2019 | CS Herediano | - | Municipal Pérez Zeledón | 4:1 |  |
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| 12. Round | 11/09/2019 | CS Herediano | - | La U Universitarios | 0:0 | ||||
| 8. Round | 16/09/2019 | AD San Carlos | - | CS Herediano | 1:0 | |
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| 13. Round | 18/09/2019 | Municipal Grecia | - | CS Herediano | 2:2 | ||||
| 14. Round | 23/09/2019 | CS Herediano | - | LD Alajuelense | 0:1 | ||||
| 15. Round | 29/09/2019 | Jicaral | - | CS Herediano | 1:2 |
Costa Rica