| 17. Jornada | 04.08.2019 | Cobreloa | - | La Serena | 3:1 | ||||
| 18. Jornada | 12.08.2019 | San Luis | - | Cobreloa | 1:1 | ||||
| 20. Jornada | 25.08.2019 | Cobreloa | - | Unión San Felipe | 1:0 |  |
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| 21. Jornada | 31.08.2019 | Cobreloa | - | Deportes Melipilla | 0:1 | ||||
| 22. Jornada | 08.09.2019 | Puerto Montt | - | Cobreloa | 1:1 | ||||
| 24. Jornada | 29.09.2019 | Deportes Temuco | - | Cobreloa | 2:1 | ||||
| 25. Jornada | 06.10.2019 | Cobreloa | - | Deportes Valdivia | 2:1 | ||||
| 26. Jornada | 13.10.2019 | Santiago Wanderers | - | Cobreloa | 5:1 |
Chile