| 1. Jornada | 12.01.2020 | Municipal Grecia | - | CS Herediano | 3:3 | ||||
| 2. Jornada | 16.01.2020 | CS Herediano | - | Jicaral | 1:0 | ||||
| 3. Jornada | 19.01.2020 | LD Alajuelense | - | CS Herediano | 0:0 | ||||
| 5. Jornada | 26.01.2020 | CS Herediano | - | Deportivo Saprissa | 4:1 | ||||
| 9. Jornada | 13.02.2020 | CS Herediano | - | CS Cartaginés | 3:0 |  |
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| 10. Jornada | 16.02.2020 | CS Herediano | - | AD San Carlos | 3:3 | |
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| 12. Jornada | 29.02.2020 | Municipal Grecia | - | CS Herediano | 0:0 | ||||
| 14. Jornada | 09.03.2020 | CS Herediano | - | LD Alajuelense | 3:3 | ||||
| 15. Jornada | 16.03.2020 | CS Herediano | - | Limón FC | 0:1 | |
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| 21. Jornada | 08.06.2020 | AD San Carlos | - | CS Herediano | 1:3 | |
Costa Rica