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| 1st(1st leg) | CS Herediano | - | Deportivo Saprissa | 1:1 (0:1) | ||
| 2nd (2nd leg) | Deportivo Saprissa | - | CS Herediano | 4:5 (1:0, 1:1, 1:1) pso | ||
| 1st(1st leg): 24/11/2019 02:00 | 2nd (2nd leg): 01/12/2019 22:00 | Winner: CS Herediano | ||||
| 1st(1st leg) | AD San Carlos | - | LD Alajuelense | 0:0 (0:0) | ||
| 2nd (2nd leg) | LD Alajuelense | - | AD San Carlos | 3:0 (2:0) | ||
| 1st(1st leg): 25/11/2019 00:00 | 2nd (2nd leg): 01/12/2019 00:00 | Winner: LD Alajuelense | ||||
