| 1. Round | 29/07/2021 | CS Herediano | - | Guadalupe | 0:1 |  |
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| 2. Round | 01/08/2021 | Guadalupe | - | AD San Carlos | 1:1 | ||||
| 3. Round | 07/08/2021 | AD Guanacasteca | - | Guadalupe | 0:1 | ||||
| 4. Round | 11/08/2021 | Guadalupe | - | Deportivo Saprissa | 1:1 | ||||
| 5. Round | 15/08/2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 | ||||
| 6. Round | 18/08/2021 | Guadalupe | - | Sporting FC | 2:2 | ||||
| 7. Round | 25/08/2021 | CS Cartaginés | - | Guadalupe | 0:1 | |
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| 8. Round | 28/08/2021 | Jicaral | - | Guadalupe | 0:0 | ||||
| 9. Round | 07/09/2021 | Guadalupe | - | Municipal Grecia | 0:2 |  |
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| 11. Round | 17/09/2021 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| 12. Round | 19/09/2021 | Guadalupe | - | CS Herediano | 0:2 | ||||
| 13. Round | 26/09/2021 | AD San Carlos | - | Guadalupe | 4:2 |
Costa Rica