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| H | Santiago City | - | Aguará | 9:1 (5:0) | ||
| R | Aguará | - | Santiago City | 1:2 | ||
| H: 11.03.2023 00:00 | R: 18.03.2023 00:00 | Sieger: Santiago City | ||||
| H | Municipal Puente Alto | - | Deportes Colina | 0:3 | ||
| R | Deportes Colina | - | Municipal Puente Alto | 1:0 | ||
| H: 11.03.2023 00:00 | R: 18.03.2023 22:00 | Sieger: Deportes Colina | ||||
| H | Rancagua Sur | - | Chimbarongo | 1:0 | ||
| R | Chimbarongo | - | Rancagua Sur | 3:1 (0:1) | ||
| H: 11.03.2023 00:00 | R: 18.03.2023 00:00 | Sieger: Chimbarongo | ||||
| H | Quintero Unido | - | Concón National | 1:0 | ||
| R | Concón National | - | Quintero Unido | 3:3 | ||
| H: 11.03.2023 21:30 | R: 19.03.2023 21:30 | Sieger: Quintero Unido | ||||
| H | Comunal Cabrero | - | Provincial Ranco | 2:1 | ||
| R | Provincial Ranco | - | Comunal Cabrero | 0:1 | ||
| H: 11.03.2023 21:30 | R: 18.03.2023 22:00 | Sieger: Comunal Cabrero | ||||
| H | Deportes Quillón | - | Colchagua | 1:4 | ||
| R | Colchagua | - | Deportes Quillón | 0:0 | ||
| H: 11.03.2023 22:00 | R: 19.03.2023 21:30 | Sieger: Colchagua | ||||
| H | Provincial Ovalle | - | Brujas de Salamanca | 5:0 | ||
| R | Brujas de Salamanca | - | Provincial Ovalle | 1:2 | ||
| H: 11.03.2023 23:00 | R: 19.03.2023 21:30 | Sieger: Provincial Ovalle | ||||
