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| 1st(1st leg) | La Serena | - | Deportes Temuco | 1:0 (1:0) | ||
| 2nd (2nd leg) | Deportes Temuco | - | La Serena | 3:1 (1:0, 1:0) pso | ||
| 1st(1st leg): 08/11/2023 21:00 | 2nd (2nd leg): 14/11/2023 23:30 | Winner: Deportes Temuco | ||||
| 1st(1st leg) | San Luis | - | Antofagasta | 1:1 (0:1) | ||
| 2nd (2nd leg) | Antofagasta | - | San Luis | 6:5 (0:0, 1:1) pso | ||
| 1st(1st leg): 09/11/2023 21:00 | 2nd (2nd leg): 14/11/2023 21:00 | Winner: Antofagasta | ||||
| 1st(1st leg) | Unión San Felipe | - | Santiago Wanderers | 2:1 (0:1) | ||
| 2nd (2nd leg) | Santiago Wanderers | - | Unión San Felipe | 2:0 (1:0) | ||
| 1st(1st leg): 10/11/2023 22:00 | 2nd (2nd leg): 15/11/2023 22:00 | Winner: Santiago Wanderers | ||||
