| Primera | 29/07/19 | Guadalupe | - | Municipal Pérez Zeledón | 1:2 |  |
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| Primera | 22/09/19 | Municipal Pérez Zeledón | - | Guadalupe | 0:1 |  |
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| Primera | 05/11/20 | Santos de Guápiles | - | Guadalupe | 1:1 | |
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| Primera | 01/02/21 | Santos de Guápiles | - | Guadalupe | 2:2 | ||||
| Primera | 04/04/21 | Guadalupe | - | Santos de Guápiles | 2:4 | ||||
| Primera | 01/08/21 | Guadalupe | - | AD San Carlos | 1:1 | ||||
| Primera | 30/10/21 | Guadalupe | - | Jicaral | 2:0 | ||||
| Primera | 12/02/22 | Jicaral | - | Guadalupe | 2:0 | |
Costa Rica