| 1. Jornada | 29.07.2021 | CS Herediano | - | Guadalupe | 0:1 |  |
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| 2. Jornada | 01.08.2021 | Guadalupe | - | AD San Carlos | 1:1 | ||||
| 3. Jornada | 07.08.2021 | AD Guanacasteca | - | Guadalupe | 0:1 | ||||
| 4. Jornada | 11.08.2021 | Guadalupe | - | Deportivo Saprissa | 1:1 | ||||
| 5. Jornada | 15.08.2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 | ||||
| 6. Jornada | 18.08.2021 | Guadalupe | - | Sporting FC | 2:2 | ||||
| 7. Jornada | 25.08.2021 | CS Cartaginés | - | Guadalupe | 0:1 | |
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| 8. Jornada | 28.08.2021 | Jicaral | - | Guadalupe | 0:0 | ||||
| 9. Jornada | 08.09.2021 | Guadalupe | - | Municipal Grecia | 0:2 |  |
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| 11. Jornada | 17.09.2021 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| 12. Jornada | 19.09.2021 | Guadalupe | - | CS Herediano | 0:2 | ||||
| 13. Jornada | 26.09.2021 | AD San Carlos | - | Guadalupe | 4:2 |
Costa Rica