| 4. Ronde | 09.03.2019 | La Serena | - | Cobreloa | 1:2 | ||||
| 7. Ronde | 07.04.2019 | Cobreloa | - | Puerto Montt | 2:1 | ||||
| 10. Ronde | 28.04.2019 | Cobreloa | - | Santiago Wanderers | 4:1 | ||||
| 11. Ronde | 05.05.2019 | Ñublense | - | Cobreloa | 3:2 | ||||
| 12. Ronde | 12.05.2019 | Cobreloa | - | Santiago Morning | 3:0 |  |
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| 13. Ronde | 17.05.2019 | Barnechea | - | Cobreloa | 0:1 | ||||
| 14. Ronde | 25.05.2019 | Cobreloa | - | CD Magallanes | 0:0 | ||||
| 16. Ronde | 27.07.2019 | Deportes Copiapó | - | Cobreloa | 2:1 | ||||
| 19. Ronde | 19.08.2019 | Santiago Morning | - | Cobreloa | 1:1 | ||||
| 20. Ronde | 25.08.2019 | Cobreloa | - | Unión San Felipe | 1:0 | |
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| 22. Ronde | 08.09.2019 | Puerto Montt | - | Cobreloa | 1:1 | ||||
| 24. Ronde | 29.09.2019 | Deportes Temuco | - | Cobreloa | 2:1 | |
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| 25. Ronde | 06.10.2019 | Cobreloa | - | Deportes Valdivia | 2:1 | ||||
| 26. Ronde | 13.10.2019 | Santiago Wanderers | - | Cobreloa | 5:1 | |
Chili