| 1. Jornada | 21.07.2019 | La U Universitarios | - | CS Herediano | 0:1 |  |
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| 2. Jornada | 25.07.2019 | CS Herediano | - | Municipal Grecia | 3:0 | ||||
| 3. Jornada | 28.07.2019 | LD Alajuelense | - | CS Herediano | 3:2 | |
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| 4. Jornada | 04.08.2019 | CS Herediano | - | Jicaral | 1:2 | ||||
| 6. Jornada | 15.08.2019 | CS Herediano | - | Limón FC | 3:2 | ||||
| 10. Jornada | 05.09.2019 | Santos de Guápiles | - | CS Herediano | 1:1 | |
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| 11. Jornada | 08.09.2019 | CS Herediano | - | Municipal Pérez Zeledón | 4:1 | |
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| 12. Jornada | 11.09.2019 | CS Herediano | - | La U Universitarios | 0:0 | ||||
| 8. Jornada | 16.09.2019 | AD San Carlos | - | CS Herediano | 1:0 | ||||
| 13. Jornada | 18.09.2019 | Municipal Grecia | - | CS Herediano | 2:2 | ||||
| 14. Jornada | 23.09.2019 | CS Herediano | - | LD Alajuelense | 0:1 |
Costa Rica