| 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 | ||||
| 5. Jornada | 12.08.2019 | CS Cartaginés | - | CS Herediano | 1:1 | ||||
| 7. Jornada | 18.08.2019 | CS Herediano | - | Guadalupe | 2:0 |  |
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| 10. Jornada | 05.09.2019 | Santos de Guápiles | - | CS Herediano | 1:1 | ||||
| 14. Jornada | 23.09.2019 | CS Herediano | - | LD Alajuelense | 0:1 | ||||
| 15. Jornada | 29.09.2019 | Jicaral | - | CS Herediano | 1:2 | |
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| 16. Jornada | 07.10.2019 | CS Herediano | - | CS Cartaginés | 3:0 | |
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| 17. Jornada | 09.10.2019 | Limón FC | - | CS Herediano | 1:0 | |
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| 9. Jornada | 13.10.2019 | CS Herediano | - | Deportivo Saprissa | 4:0 | |
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| 18. Jornada | 17.10.2019 | Guadalupe | - | CS Herediano | 1:1 | ||||
| 19. Jornada | 20.10.2019 | CS Herediano | - | AD San Carlos | 3:1 | |
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| 20. Jornada | 27.10.2019 | Deportivo Saprissa | - | CS Herediano | 2:1 | ||||
| 21. Jornada | 03.11.2019 | CS Herediano | - | Santos de Guápiles | 6:2 | |
México