| 1. Round | 21/07/2019 | La U Universitarios | - | CS Herediano | 0:1 | ||||
| 2. Round | 25/07/2019 | CS Herediano | - | Municipal Grecia | 3:0 |  |
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| 4. Round | 04/08/2019 | CS Herediano | - | Jicaral | 1:2 | ||||
| 11. Round | 08/09/2019 | CS Herediano | - | Municipal Pérez Zeledón | 4:1 | ||||
| 8. Round | 16/09/2019 | AD San Carlos | - | CS Herediano | 1:0 | ||||
| 15. Round | 29/09/2019 | Jicaral | - | CS Herediano | 1:2 |  |
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| 9. Round | 13/10/2019 | CS Herediano | - | Deportivo Saprissa | 4:0 | ||||
| 19. Round | 20/10/2019 | CS Herediano | - | AD San Carlos | 3:1 | ||||
| 22. Round | 16/11/2019 | Municipal Pérez Zeledón | - | CS Herediano | 1:0 |
Costa Rica