| Primera | 08/03/20 | Santos de Guápiles | - | Guadalupe | 3:4 |  |
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| Primera | 30/05/20 | Municipal Grecia | - | Guadalupe | 2:0 |  |
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| Primera | 04/10/20 | Guadalupe | - | LD Alajuelense | 1:2 | ||||
| Primera | 11/11/20 | Limón FC | - | Guadalupe | 2:1 | ||||
| Primera | 04/03/21 | Guadalupe | - | LD Alajuelense | 1:3 |  |
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| Primera | 26/01/23 | Sporting FC | - | Guadalupe | 2:0 | ||||
| Primera | 12/02/23 | Guadalupe | - | AD Guanacasteca | 1:1 | ||||
| Primera | 16/04/23 | AD Guanacasteca | - | Guadalupe | 2:0 |
Argentina