| 1. Jornada | 21.07.2019 | La U Universitarios | - | CS Herediano | 0:1 | ||||
| 2. Jornada | 25.07.2019 | CS Herediano | - | Municipal Grecia | 3:0 | ||||
| 3. Jornada | 28.07.2019 | LD Alajuelense | - | CS Herediano | 3:2 | ||||
| 4. Jornada | 04.08.2019 | CS Herediano | - | Jicaral | 1:2 | ||||
| 5. Jornada | 12.08.2019 | CS Cartaginés | - | CS Herediano | 1:1 |  |
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| 6. Jornada | 15.08.2019 | CS Herediano | - | Limón FC | 3:2 | ||||
| 10. Jornada | 05.09.2019 | Santos de Guápiles | - | CS Herediano | 1:1 | ||||
| 11. Jornada | 08.09.2019 | CS Herediano | - | Municipal Pérez Zeledón | 4:1 | ||||
| 12. Jornada | 11.09.2019 | CS Herediano | - | La U Universitarios | 0:0 | ||||
| 8. Jornada | 16.09.2019 | AD San Carlos | - | CS Herediano | 1:0 |  |
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| 22. Jornada | 17.11.2019 | Municipal Pérez Zeledón | - | CS Herediano | 1:0 |
Costa Rica