| 3. Round | 28/07/2019 | CS Cartaginés | - | AD San Carlos | 1:0 | ||||
| 9. Round | 01/09/2019 | AD San Carlos | - | Municipal Pérez Zeledón | 5:2 | ||||
| 13. Round | 18/09/2019 | La U Universitarios | - | AD San Carlos | 1:1 | ||||
| 15. Round | 29/09/2019 | Municipal Grecia | - | AD San Carlos | 1:1 | ||||
| 17. Round | 12/10/2019 | Santos de Guápiles | - | AD San Carlos | 1:3 |  |
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| 18. Round | 16/10/2019 | AD San Carlos | - | Limón FC | 2:2 | |
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| 19. Round | 20/10/2019 | CS Herediano | - | AD San Carlos | 3:1 | ||||
| 20. Round | 27/10/2019 | Municipal Pérez Zeledón | - | AD San Carlos | 3:0 | |
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| 21. Round | 03/11/2019 | AD San Carlos | - | LD Alajuelense | 3:1 |
Costa Rica