| 6. Jornada | 15.08.2019 | CS Herediano | - | Limón FC | 3:2 |  |
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| 7. Jornada | 18.08.2019 | CS Herediano | - | Guadalupe | 2:0 | ||||
| 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 | ||||
| 15. Jornada | 29.09.2019 | Jicaral | - | CS Herediano | 1:2 | ||||
| 17. Jornada | 09.10.2019 | Limón FC | - | CS Herediano | 1:0 | ||||
| 18. Jornada | 17.10.2019 | Guadalupe | - | CS Herediano | 1:1 | ||||
| 21. Jornada | 03.11.2019 | CS Herediano | - | Santos de Guápiles | 6:2 |  |
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| 22. Jornada | 17.11.2019 | Municipal Pérez Zeledón | - | CS Herediano | 1:0 |
México