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| 1st(1st leg) | Cobreloa | - | Colo-Colo | 2:2 (1:1) | ||
| 2nd (2nd leg) | Colo-Colo | - | Cobreloa | 1:0 (0:0) | ||
| 1st(1st leg): 27/09/2023 22:00 | 2nd (2nd leg): 04/10/2023 23:00 | Winner: Colo-Colo | ||||
| 1st(1st leg) | Universidad de Concepción | - | CD Magallanes | 1:3 (0:2) | ||
| 2nd (2nd leg) | CD Magallanes | - | Universidad de Concepción | 1:2 (1:1) | ||
| 1st(1st leg): 28/09/2023 00:30 | 2nd (2nd leg): 04/10/2023 19:30 | Winner: CD Magallanes | ||||
