| 1. Jornada | 21.07.2019 | Guadalupe | - | LD Alajuelense | 1:1 | ||||
| 2. Jornada | 25.07.2019 | Santos de Guápiles | - | Guadalupe | 0:2 | ||||
| 3. Jornada | 29.07.2019 | Guadalupe | - | Municipal Pérez Zeledón | 1:2 |  |
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| 4. Jornada | 04.08.2019 | Deportivo Saprissa | - | Guadalupe | 4:1 | |
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| 5. Jornada | 12.08.2019 | Guadalupe | - | Limón FC | 4:3 | |
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| 6. Jornada | 15.08.2019 | La U Universitarios | - | Guadalupe | 2:2 | ||||
| 7. Jornada | 18.08.2019 | CS Herediano | - | Guadalupe | 2:0 | ||||
| 8. Jornada | 25.08.2019 | Guadalupe | - | Jicaral | 1:1 | ||||
| 10. Jornada | 06.09.2019 | Guadalupe | - | CS Cartaginés | 1:0 | |
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| 11. Jornada | 08.09.2019 | AD San Carlos | - | Guadalupe | 3:1 | ||||
| 12. Jornada | 14.09.2019 | LD Alajuelense | - | Guadalupe | 2:1 | |
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| 20. Jornada | 27.10.2019 | Guadalupe | - | Municipal Grecia | 2:1 |
Costa Rica