| 1. Ronde | 11.01.2020 | Guadalupe | - | La U Universitarios | 5:0 | ||||
| 2. Ronde | 17.01.2020 | Deportivo Saprissa | - | Guadalupe | 3:0 | ||||
| 10. Ronde | 16.02.2020 | Jicaral | - | Guadalupe | 0:0 |  |
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| 3. Ronde | 20.02.2020 | Guadalupe | - | Santos de Guápiles | 1:0 | ||||
| 11. Ronde | 22.02.2020 | Guadalupe | - | CS Cartaginés | 0:0 | ||||
| 12. Ronde | 01.03.2020 | La U Universitarios | - | Guadalupe | 3:0 | ||||
| 13. Ronde | 06.03.2020 | Guadalupe | - | Deportivo Saprissa | 2:1 | |
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| 14. Ronde | 09.03.2020 | Santos de Guápiles | - | Guadalupe | 3:4 | ||||
| 15. Ronde | 16.03.2020 | AD San Carlos | - | Guadalupe | 2:2 | |
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| 16. Ronde | 19.05.2020 | Guadalupe | - | Limón FC | 1:0 | ||||
| 17. Ronde | 25.05.2020 | CS Herediano | - | Guadalupe | 0:0 | |
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| 22. Ronde | 11.06.2020 | CS Cartaginés | - | Guadalupe | 0:0 | |
Costa Rica