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| 1st(1st leg) | Santiago City | - | Aguará | 9:1 (5:0) | ||
| 2nd (2nd leg) | Aguará | - | Santiago City | 1:2 | ||
| 1st(1st leg): 10/03/2023 23:00 | 2nd (2nd leg): 17/03/2023 23:00 | Winner: Santiago City | ||||
| 1st(1st leg) | Municipal Puente Alto | - | Deportes Colina | 0:3 | ||
| 2nd (2nd leg) | Deportes Colina | - | Municipal Puente Alto | 1:0 | ||
| 1st(1st leg): 10/03/2023 23:00 | 2nd (2nd leg): 18/03/2023 21:00 | Winner: Deportes Colina | ||||
| 1st(1st leg) | Rancagua Sur | - | Chimbarongo | 1:0 | ||
| 2nd (2nd leg) | Chimbarongo | - | Rancagua Sur | 3:1 (0:1) | ||
| 1st(1st leg): 10/03/2023 23:00 | 2nd (2nd leg): 17/03/2023 23:00 | Winner: Chimbarongo | ||||
| 1st(1st leg) | Quintero Unido | - | Concón National | 1:0 | ||
| 2nd (2nd leg) | Concón National | - | Quintero Unido | 3:3 | ||
| 1st(1st leg): 11/03/2023 20:30 | 2nd (2nd leg): 19/03/2023 20:30 | Winner: Quintero Unido | ||||
| 1st(1st leg) | Comunal Cabrero | - | Provincial Ranco | 2:1 | ||
| 2nd (2nd leg) | Provincial Ranco | - | Comunal Cabrero | 0:1 | ||
| 1st(1st leg): 11/03/2023 20:30 | 2nd (2nd leg): 18/03/2023 21:00 | Winner: Comunal Cabrero | ||||
| 1st(1st leg) | Deportes Quillón | - | Colchagua | 1:4 | ||
| 2nd (2nd leg) | Colchagua | - | Deportes Quillón | 0:0 | ||
| 1st(1st leg): 11/03/2023 21:00 | 2nd (2nd leg): 19/03/2023 20:30 | Winner: Colchagua | ||||
| 1st(1st leg) | Provincial Ovalle | - | Brujas de Salamanca | 5:0 | ||
| 2nd (2nd leg) | Brujas de Salamanca | - | Provincial Ovalle | 1:2 | ||
| 1st(1st leg): 11/03/2023 22:00 | 2nd (2nd leg): 19/03/2023 20:30 | Winner: Provincial Ovalle | ||||
