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| 22.06.2023 | 01:00 | Universidad de Chile | - | O'Higgins | 3:5 (0:0, 0:0) i.E. | |
| 21:00 | Palestino | - | Santiago Morning | 5:4 (2:2) | ||
| 23.06.2023 | 01:00 | Audax Italiano | - | Rengo | 2:1 (1:0) | |
| 01:00 | Cobresal | - | Deportes Copiapó | 3:0 (1:0) | ||
| 24.06.2023 | 18:30 | Coquimbo Unido | - | La Serena | 4:2 (0:0, 1:1) i.E. | |
| 25.06.2023 | 21:00 | Puerto Montt | - | Provincial Osorno | 1:0 (0:0) | |
| 23:30 | Cobreloa | - | Antofagasta | 2:0 (1:0) | ||
| 26.06.2023 | 18:30 | Deportes Iquique | - | San Marcos | 0:4 (0:0) | |
| 29.06.2023 | 00:00 | Huachipato | - | Deportes Temuco | 3:4 (1:1, 2:2) i.E. | |
| 01.07.2023 | 01:00 | Unión Española | - | Barnechea | 2:0 (1:0) | |
| 02.07.2023 | 00:00 | Everton | - | Unión San Felipe | 5:1 (2:1) | |
| 18:30 | Universidad de Concepción | - | Fernández Vial | 1:0 (0:0) | ||
| 03.07.2023 | 00:00 | Universidad Católica | - | Santiago Wanderers | 2:0 (1:0) | |
| 04.07.2023 | 22:00 | Rangers | - | Comunal Cabrero | 1:0 (1:0) | |
| 05.07.2023 | 01:00 | Colo-Colo | - | Unión La Calera | 6:1 (4:0) | |
| 12.07.2023 | 21:00 | CD Magallanes | - | Santa Cruz | 3:0 (3:0) |
