| 1. Round | 21/07/2019 | AD San Carlos | - | Deportivo Saprissa | 1:0 | ||||
| 3. Round | 28/07/2019 | CS Cartaginés | - | AD San Carlos | 1:0 |  |
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| 6. Round | 15/08/2019 | AD San Carlos | - | Santos de Guápiles | 2:2 | ||||
| 7. Round | 17/08/2019 | Limón FC | - | AD San Carlos | 3:4 | ||||
| 9. Round | 01/09/2019 | AD San Carlos | - | Municipal Pérez Zeledón | 5:2 |  |
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| 10. Round | 05/09/2019 | LD Alajuelense | - | AD San Carlos | 1:0 | ||||
| 8. Round | 16/09/2019 | AD San Carlos | - | CS Herediano | 1:0 | |
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| 14. Round | 23/09/2019 | AD San Carlos | - | CS Cartaginés | 2:4 | ||||
| 16. Round | 07/10/2019 | AD San Carlos | - | Jicaral | 2:1 | ||||
| 18. Round | 16/10/2019 | AD San Carlos | - | Limón FC | 2:2 | ||||
| 19. Round | 20/10/2019 | CS Herediano | - | AD San Carlos | 3:1 | |
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| 21. Round | 03/11/2019 | AD San Carlos | - | LD Alajuelense | 3:1 | ||||
| 22. Round | 21/11/2019 | Guadalupe | - | AD San Carlos | 2:2 |
Costa Rica