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| 1st(1st leg) | Once Caldas | - | Independiente Medellín | 2:3 (1:1) | ||
| 2nd (2nd leg) | Independiente Medellín | - | Once Caldas | 1:0 (0:0) | ||
| 1st(1st leg): 29/08/2019 01:30 | 2nd (2nd leg): 12/09/2019 02:15 | Winner: Independiente Medellín | ||||
| 1st(1st leg) | Deportivo Pasto | - | Deportivo Pereira | 4:0 (2:0) | ||
| 2nd (2nd leg) | Deportivo Pereira | - | Deportivo Pasto | 2:0 (1:0) | ||
| 1st(1st leg): 29/08/2019 20:00 | 2nd (2nd leg): 13/09/2019 00:00 | Winner: Deportivo Pasto | ||||
| 1st(1st leg) | Atlético Nacional | - | Deportes Tolima | 0:1 (0:0) | ||
| 2nd (2nd leg) | Deportes Tolima | - | Atlético Nacional | 1:1 (0:1) | ||
| 1st(1st leg): 30/08/2019 00:00 | 2nd (2nd leg): 12/09/2019 00:00 | Winner: Deportes Tolima | ||||
| 1st(1st leg) | Deportivo Cali | - | Atlético Junior | 2:1 (0:1) | ||
| 2nd (2nd leg) | Atlético Junior | - | Deportivo Cali | 3:4 (1:1, 2:1, 2:1) pso | ||
| 1st(1st leg): 30/08/2019 02:00 | 2nd (2nd leg): 13/09/2019 02:15 | Winner: Deportivo Cali | ||||
