| 2. Round | 15/01/2020 | Limón FC | - | AD San Carlos | 1:2 |  |
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| 3. Round | 20/01/2020 | AD San Carlos | - | Municipal Pérez Zeledón | 3:2 | ||||
| 4. Round | 23/01/2020 | Guadalupe | - | AD San Carlos | 0:2 | ||||
| 5. Round | 26/01/2020 | Jicaral | - | AD San Carlos | 2:1 | ||||
| 7. Round | 06/02/2020 | Santos de Guápiles | - | AD San Carlos | 5:2 | ||||
| 8. Round | 09/02/2020 | CS Cartaginés | - | AD San Carlos | 3:2 | ||||
| 9. Round | 13/02/2020 | AD San Carlos | - | La U Universitarios | 2:2 | |
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| 11. Round | 22/02/2020 | AD San Carlos | - | Municipal Grecia | 1:0 | ||||
| 12. Round | 02/03/2020 | Deportivo Saprissa | - | AD San Carlos | 5:3 | ||||
| 13. Round | 05/03/2020 | AD San Carlos | - | Limón FC | 1:1 | |
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| 16. Round | 21/05/2020 | AD San Carlos | - | Jicaral | 0:1 |  |
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| 19. Round | 31/05/2020 | AD San Carlos | - | CS Cartaginés | 1:3 | ||||
| 20. Round | 03/06/2020 | La U Universitarios | - | AD San Carlos | 1:2 | ||||
| 21. Round | 08/06/2020 | AD San Carlos | - | CS Herediano | 1:3 | ||||
| 22. Round | 10/06/2020 | Municipal Grecia | - | AD San Carlos | 2:5 | |
Costa Rica