[3] Santa Ana 3-1 Guadalupe FC [9] 2023-08-05 20:30
Stadium: Estadio Piedades de Santa Ana Pitch: Excellent Round: 2
Home History
| Costa Rica Segunda | 2023/07/30 21:00 | Limon Black Star v Santa Ana | W | 1-2 |
| Costa Rica Segunda | 2023/04/23 20:00 | Santa Ana v Quepos Cambute FC | L | 0-1 |
| Costa Rica Segunda | 2023/04/16 18:30 | Quepos Cambute FC v Santa Ana | D | 3-3 |
| Costa Rica Segunda | 2023/04/09 20:00 | Santa Ana v Escorpiones de Belen FC | W | 2-0 |
| Costa Rica Segunda | 2023/03/26 22:00 | Santa Ana v Limon Black Star | D | 1-1 |
| Costa Rica Segunda | 2023/03/22 17:00 | Municipal Turrialba v Santa Ana | W | 0-3 |
| Costa Rica Segunda | 2023/03/19 01:00 | Santa Ana v CS Uruguay de Coronado | D | 2-2 |
| Costa Rica Segunda | 2023/03/12 21:00 | FC Aserri v Santa Ana | W | 1-2 |
Away History
| Costa Rica Segunda | 2023/07/29 19:00 | Guadalupe FC v Escorpiones de Belen FC | L | 0-3 |
| Club Friendly List | 2023/07/14 01:00 | Guadalupe FC v Deportivo Saprissa | D | 2-2 |
| Costa Rica Primera Division | 2023/05/07 21:00 | Guadalupe FC v Alajuelense | W | 3-2 |
| Costa Rica Primera Division | 2023/04/29 23:00 | Santos de Guápiles v Guadalupe FC | W | 1-3 |
| Costa Rica Primera Division | 2023/04/23 01:00 | Municipal Perez Zeledon v Guadalupe FC | L | 3-1 |
| Costa Rica Primera Division | 2023/04/19 23:00 | Guadalupe FC v AD San Carlos | L | 2-3 |
| Costa Rica Primera Division | 2023/04/16 21:00 | AD Guanacasteca v Guadalupe FC | L | 2-0 |
| Costa Rica Primera Division | 2023/04/11 01:00 | Guadalupe FC v AD Grecia | D | 1-1 |