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| 1st(1st leg) | Unión Compañías | - | Brujas de Salamanca | 1:1 (1:1) | ||
| 2nd (2nd leg) | Brujas de Salamanca | - | Unión Compañías | 2:0 (1:0) | ||
| 1st(1st leg): 27/04/2024 17:00 | 2nd (2nd leg): 04/05/2024 01:00 | Winner: Brujas de Salamanca | ||||
| 1st(1st leg) | Deportes Quillón | - | Constitución Unido | 4:3 (1:2) | ||
| 2nd (2nd leg) | Constitución Unido | - | Deportes Quillón | 1:1 (0:0) | ||
| 1st(1st leg): 27/04/2024 17:00 | 2nd (2nd leg): 01/05/2024 21:00 | Winner: Deportes Quillón | ||||
| 1st(1st leg) | Municipal Mejillones | - | Deportes Colina | 0:1 (0:0) | ||
| 2nd (2nd leg) | Deportes Colina | - | Municipal Mejillones | 2:3 (0:0, 0:1, 0:1) pso | ||
| 1st(1st leg): 27/04/2024 21:00 | 2nd (2nd leg): 04/05/2024 21:00 | Winner: Municipal Mejillones | ||||
| 1st(1st leg) | Chimbarongo | - | Santiago City | 4:2 (1:0) | ||
| 2nd (2nd leg) | Santiago City | - | Chimbarongo | 4:1 (1:0, 4:0, 4:0) pso | ||
| 1st(1st leg): 27/04/2024 21:00 | 2nd (2nd leg): 03/05/2024 22:00 | Winner: Santiago City | ||||
| 1st(1st leg) | Comunal Cabrero | - | Deportes Iberia | 1:0 (1:0) | ||
| 2nd (2nd leg) | Deportes Iberia | - | Comunal Cabrero | 4:5 (0:1, 2:1, 2:1) pso | ||
| 1st(1st leg): 27/04/2024 21:00 | 2nd (2nd leg): 05/05/2024 20:00 | Winner: Comunal Cabrero | ||||
| 1st(1st leg) | Unión Wanderers | - | Vicente Pérez Rosales | 0:0 | ||
| 2nd (2nd leg) | Vicente Pérez Rosales | - | Unión Wanderers | 4:1 (1:1, 1:1, 1:1) pso | ||
| 1st(1st leg): 27/04/2024 22:00 | 2nd (2nd leg): 04/05/2024 20:00 | Winner: Vicente Pérez Rosales | ||||
| 1st(1st leg) | Imperial Unido | - | Deportes Valdivia | 1:0 (0:0) | ||
| 2nd (2nd leg) | Deportes Valdivia | - | Imperial Unido | 0:0 | ||
| 1st(1st leg): 28/04/2024 01:00 | 2nd (2nd leg): 04/05/2024 21:00 | Winner: Imperial Unido | ||||
| 1st(1st leg) | San Antonio Unido Temuco | - | Ferroviarios de Monte Aguila | 3:1 (2:0) | ||
| 2nd (2nd leg) | Ferroviarios de Monte Aguila | - | San Antonio Unido Temuco | 1:2 (0:1) | ||
| 1st(1st leg): 28/04/2024 20:00 | 2nd (2nd leg): 04/05/2024 20:00 | Winner: San Antonio Unido Temuco | ||||
| 1st(1st leg) | Glorias Navales | - | Miramar de Coquimbo | 1:1 (1:1) | ||
| 2nd (2nd leg) | Miramar de Coquimbo | - | Glorias Navales | 0:2 (0:1) | ||
| 1st(1st leg): 28/04/2024 22:00 | 2nd (2nd leg): 05/05/2024 20:00 | Winner: Glorias Navales | ||||
| 1st(1st leg) | Colchagua | - | Municipal Puente Alto | 2:2 (2:1) | ||
| 2nd (2nd leg) | Municipal Puente Alto | - | Colchagua | 3:2 (0:1) | ||
| 1st(1st leg): 28/04/2024 23:00 | 2nd (2nd leg): 04/05/2024 23:30 | Winner: Municipal Puente Alto | ||||
| 1st(1st leg) | El Lucero de Chillán | - | Juvenil Seminario de Talca | 1:3 (0:2) | ||
| 2nd (2nd leg) | Juvenil Seminario de Talca | - | El Lucero de Chillán | 1:0 (0:0) | ||
| 1st(1st leg): 30/04/2024 00:00 | 2nd (2nd leg): 05/05/2024 00:00 | Winner: Juvenil Seminario de Talca | ||||
