| 1. Jornada | 21.07.2019 | Guadalupe | - | LD Alajuelense | 1:1 |  |
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| 2. Jornada | 25.07.2019 | Santos de Guápiles | - | Guadalupe | 0:2 | |
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| 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 | |
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| 7. Jornada | 18.08.2019 | CS Herediano | - | Guadalupe | 2:0 | |
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| 8. Jornada | 25.08.2019 | Guadalupe | - | Jicaral | 1:1 | |
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| 9. Jornada | 01.09.2019 | Municipal Grecia | - | Guadalupe | 2:1 | |
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| 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 | |
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| 12. Jornada | 14.09.2019 | LD Alajuelense | - | Guadalupe | 2:1 | |
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| 13. Jornada | 19.09.2019 | Guadalupe | - | Santos de Guápiles | 2:4 | |
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| 15. Jornada | 29.09.2019 | Guadalupe | - | Deportivo Saprissa | 2:1 | ||||
| 16. Jornada | 06.10.2019 | Limón FC | - | Guadalupe | 2:1 | |
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| 17. Jornada | 11.10.2019 | Guadalupe | - | La U Universitarios | 1:0 | |
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| 21. Jornada | 03.11.2019 | CS Cartaginés | - | Guadalupe | 2:1 | ||||
| 22. Jornada | 21.11.2019 | Guadalupe | - | AD San Carlos | 2:2 | |
Costa Rica