| 1. Round | 21/07/2019 | AD San Carlos | - | Deportivo Saprissa | 1:0 |  |
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| 2. Round | 25/07/2019 | La U Universitarios | - | AD San Carlos | 2:1 | ||||
| 5. Round | 11/08/2019 | Jicaral | - | AD San Carlos | 1:1 | ||||
| 10. Round | 05/09/2019 | LD Alajuelense | - | AD San Carlos | 1:0 | ||||
| 11. Round | 08/09/2019 | AD San Carlos | - | Guadalupe | 3:1 | |
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| 12. Round | 12/09/2019 | Deportivo Saprissa | - | AD San Carlos | 3:1 | ||||
| 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 | |
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| 15. Round | 29/09/2019 | Municipal Grecia | - | AD San Carlos | 1:1 | ||||
| 16. Round | 07/10/2019 | AD San Carlos | - | Jicaral | 2:1 |  |
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| 22. Round | 21/11/2019 | Guadalupe | - | AD San Carlos | 2:2 |
Costa Rica