| 2. Round | 25/07/2019 | La U Universitarios | - | AD San Carlos | 2:1 | ||||
| 7. Round | 17/08/2019 | Limón FC | - | AD San Carlos | 3:4 |  |
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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 | ||||
| 13. Round | 18/09/2019 | La U Universitarios | - | AD San Carlos | 1:1 | ||||
| 14. Round | 23/09/2019 | AD San Carlos | - | CS Cartaginés | 2:4 | ||||
| 20. Round | 27/10/2019 | Municipal Pérez Zeledón | - | AD San Carlos | 3:0 | ||||
| 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