| 1. Jornada | 17.02.2019 | Cobreloa | - | Deportes Temuco | 2:2 | ||||
| 2. Jornada | 23.02.2019 | Deportes Melipilla | - | Cobreloa | 1:1 |  |
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| 3. Jornada | 03.03.2019 | Cobreloa | - | Rangers | 2:2 | ||||
| 4. Jornada | 09.03.2019 | La Serena | - | Cobreloa | 1:2 | ||||
| 5. Jornada | 17.03.2019 | Cobreloa | - | Deportes Copiapó | 0:0 | ||||
| 6. Jornada | 31.03.2019 | Unión San Felipe | - | Cobreloa | 2:2 | ||||
| 9. Jornada | 21.04.2019 | Deportes Valdivia | - | Cobreloa | 2:3 | ||||
| 10. Jornada | 28.04.2019 | Cobreloa | - | Santiago Wanderers | 4:1 | ||||
| 11. Jornada | 05.05.2019 | Ñublense | - | Cobreloa | 3:2 | ||||
| 14. Jornada | 25.05.2019 | Cobreloa | - | CD Magallanes | 0:0 | ||||
| 18. Jornada | 12.08.2019 | San Luis | - | Cobreloa | 1:1 | |
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| 21. Jornada | 31.08.2019 | Cobreloa | - | Deportes Melipilla | 0:1 | |
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| 22. Jornada | 08.09.2019 | Puerto Montt | - | Cobreloa | 1:1 | |
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| 23. Jornada | 15.09.2019 | Cobreloa | - | Ñublense | 1:2 | ||||
| 24. Jornada | 29.09.2019 | Deportes Temuco | - | Cobreloa | 2:1 | |
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| 26. Jornada | 13.10.2019 | Santiago Wanderers | - | Cobreloa | 5:1 |
Chile