| 2. Jornada | 23.08.2020 | LD Alajuelense | - | Guadalupe | 0:1 |  |
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| 3. Jornada | 30.08.2020 | Municipal Pérez Zeledón | - | Guadalupe | 3:2 |  |
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| 4. Jornada | 02.09.2020 | Guadalupe | - | Municipal Grecia | 1:0 | |
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| 5. Jornada | 05.09.2020 | Guadalupe | - | CS Herediano | 2:3 | ||||
| 6. Jornada | 13.09.2020 | Municipal Grecia | - | Guadalupe | 0:1 |  |
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| 11. Jornada | 30.10.2020 | Guadalupe | - | CS Cartaginés | 1:0 | ||||
| 12. Jornada | 01.11.2020 | Jicaral | - | Guadalupe | 3:1 | ||||
| 10. Jornada | 06.11.2020 | Santos de Guápiles | - | Guadalupe | 1:1 | ||||
| 13. Jornada | 09.11.2020 | Guadalupe | - | Sporting FC | 2:2 | |
Costa Rica