| 1. Ronde | 29.07.2021 | CS Herediano | - | Guadalupe | 0:1 |  |
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| 2. Ronde | 01.08.2021 | Guadalupe | - | AD San Carlos | 1:1 | ||||
| 3. Ronde | 07.08.2021 | AD Guanacasteca | - | Guadalupe | 0:1 | ||||
| 4. Ronde | 11.08.2021 | Guadalupe | - | Deportivo Saprissa | 1:1 | ||||
| 5. Ronde | 15.08.2021 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 | ||||
| 6. Ronde | 18.08.2021 | Guadalupe | - | Sporting FC | 2:2 |  |
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| 9. Ronde | 08.09.2021 | Guadalupe | - | Municipal Grecia | 0:2 | ||||
| 10. Ronde | 12.09.2021 | Guadalupe | - | LD Alajuelense | 2:4 | ||||
| 11. Ronde | 17.09.2021 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| 12. Ronde | 19.09.2021 | Guadalupe | - | CS Herediano | 0:2 | ||||
| 21. Ronde | 25.11.2021 | LD Alajuelense | - | Guadalupe | 1:0 | ||||
| 22. Ronde | 28.11.2021 | Guadalupe | - | Santos de Guápiles | 0:5 |
Costa Rica