| 2. Round | 25/07/2019 | CS Herediano | - | Municipal Grecia | 3:0 |  |
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| 5. Round | 11/08/2019 | CS Cartaginés | - | CS Herediano | 1:1 | ||||
| 13. Round | 18/09/2019 | Municipal Grecia | - | CS Herediano | 2:2 | ||||
| 14. Round | 23/09/2019 | CS Herediano | - | LD Alajuelense | 0:1 | ||||
| 22. Round | 16/11/2019 | Municipal Pérez Zeledón | - | CS Herediano | 1:0 |
Mexico