| 2. Jornada | 23.08.2020 | LD Alajuelense | - | Guadalupe | 0:1 | ||||
| 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 |  |
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| 6. Jornada | 13.09.2020 | Municipal Grecia | - | Guadalupe | 0:1 | |
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| 7. Jornada | 20.09.2020 | CS Herediano | - | Guadalupe | 3:1 | |
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| 9. Jornada | 04.10.2020 | Guadalupe | - | LD Alajuelense | 1:2 | ||||
| 15. Jornada | 15.11.2020 | Deportivo Saprissa | - | Guadalupe | 5:1 | |
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Argentina