| 2. Round | 23/08/2020 | LD Alajuelense | - | Guadalupe | 0:1 | ||||
| 3. Round | 29/08/2020 | Municipal Pérez Zeledón | - | Guadalupe | 3:2 |  |
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| 4. Round | 02/09/2020 | Guadalupe | - | Municipal Grecia | 1:0 | |
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| 5. Round | 05/09/2020 | Guadalupe | - | CS Herediano | 2:3 |  |
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| 6. Round | 13/09/2020 | Municipal Grecia | - | Guadalupe | 0:1 | |
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| 7. Round | 20/09/2020 | CS Herediano | - | Guadalupe | 3:1 | |
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| 9. Round | 04/10/2020 | Guadalupe | - | LD Alajuelense | 1:2 | ||||
| 15. Round | 15/11/2020 | Deportivo Saprissa | - | Guadalupe | 5:1 | |
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Argentina