| Primera | 21/07/19 | Guadalupe | - | LD Alajuelense | 1:1 | ||||
| Primera | 14/09/19 | LD Alajuelense | - | Guadalupe | 2:1 | ||||
| Primera | 06/02/20 | Municipal Pérez Zeledón | - | Guadalupe | 1:1 | ||||
| Primera | 28/05/20 | Guadalupe | - | Municipal Pérez Zeledón | 3:1 |  |
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| Primera | 29/08/20 | Municipal Pérez Zeledón | - | Guadalupe | 3:2 | |
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| Primera | 21/04/21 | Guadalupe | - | Municipal Pérez Zeledón | 0:1 | ||||
| Primera | 17/10/21 | Guadalupe | - | Municipal Pérez Zeledón | 0:1 | ||||
| Primera | 02/03/22 | Municipal Pérez Zeledón | - | Guadalupe | 0:1 | ||||
| Primera | 31/07/22 | Santos de Guápiles | - | Guadalupe | 3:3 | ||||
| Primera | 28/08/22 | Guadalupe | - | Santos de Guápiles | 3:0 | ||||
| Primera | 26/02/23 | Guadalupe | - | Santos de Guápiles | 1:3 |
Costa Rica