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| 1st(1st leg) | Santa Lucía | - | Metropolitan FA | 3:0 (2:0) | ||
| 2nd (2nd leg) | Metropolitan FA | - | Santa Lucía | 1:2 (1:1) | ||
| 1st(1st leg): 04/08/2021 01:00 | 2nd (2nd leg): 18/08/2021 01:00 | Winner: Santa Lucía | ||||
| 1st(1st leg) | Diriangén FC | - | Marathón | 0:1 (0:0) | ||
| 2nd (2nd leg) | Marathón | - | Diriangén FC | 2:1 (1:0) | ||
| 1st(1st leg): 04/08/2021 03:00 | 2nd (2nd leg): 19/08/2021 03:15 | Winner: Marathón | ||||
| 1st(1st leg) | Samaritaine | - | UD Universitario | 0:3 dec. | ||
| 2nd (2nd leg) | UD Universitario | - | Samaritaine | 3:0 dec. | ||
| 1st(1st leg): 05/08/2021 01:05 | 2nd (2nd leg): 10/08/2021 23:00 | Winner: UD Universitario | ||||
| 1st(1st leg) | Hankook Verdes | - | Santos de Guápiles | 0:1 (0:0) | ||
| 2nd (2nd leg) | Santos de Guápiles | - | Hankook Verdes | 5:1 (4:0) | ||
| 1st(1st leg): 06/08/2021 01:00 | 2nd (2nd leg): 19/08/2021 01:00 | Winner: Santos de Guápiles | ||||
| 1st(1st leg) | Comunicaciones | - | Once Municipal | 1:1 (1:0) | ||
| 2nd (2nd leg) | Once Municipal | - | Comunicaciones | 0:3 (0:0) | ||
| 1st(1st leg): 06/08/2021 03:00 | 2nd (2nd leg): 20/08/2021 03:00 | Winner: Comunicaciones | ||||
| 1st(1st leg) | Forge FC | - | FAS | 3:1 (2:1) | ||
| 2nd (2nd leg) | FAS | - | Forge FC | 2:2 (1:0) | ||
| 1st(1st leg): 13/08/2021 01:00 | 2nd (2nd leg): 18/08/2021 03:15 | Winner: Forge FC | ||||
