| Date | Home | Away | Result |
|---|---|---|---|
| 12/8/23 3:00 PM | Huachipato | Audax Italiano | 2-0 |
| 12/8/23 3:00 PM | Unión Española | Cobresal | 1-0 |
| 12/8/23 3:00 PM | Curico Unido | Colo-Colo | 0-1 |
| 12/9/23 3:00 PM | O'Higgins | Palestino | 0-1 |
| 12/9/23 3:00 PM | Universidad de Chile | Ñublense | 3-1 |
| 12/9/23 3:00 PM | Unión La Calera | Universidad Católica | 0-3 |
| 12/9/23 3:00 PM | Deportes Copiapo | Everton | 2-0 |
| 12/9/23 3:00 PM | Magallanes | Coquimbo Unido | 2-3 |