| 2. Ronde | 23.02.2019 | Deportes Melipilla | - | Cobreloa | 1:1 | ||||
| 3. Ronde | 03.03.2019 | Cobreloa | - | Rangers | 2:2 | ||||
| 6. Ronde | 31.03.2019 | Unión San Felipe | - | Cobreloa | 2:2 |  |
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| 7. Ronde | 07.04.2019 | Cobreloa | - | Puerto Montt | 2:1 | ||||
| 8. Ronde | 14.04.2019 | Cobreloa | - | San Luis | 3:0 | ||||
| 9. Ronde | 21.04.2019 | Deportes Valdivia | - | Cobreloa | 2:3 | ||||
| 10. Ronde | 28.04.2019 | Cobreloa | - | Santiago Wanderers | 4:1 | ||||
| 19. Ronde | 19.08.2019 | Santiago Morning | - | Cobreloa | 1:1 | |
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| 20. Ronde | 25.08.2019 | Cobreloa | - | Unión San Felipe | 1:0 | ||||
| 21. Ronde | 31.08.2019 | Cobreloa | - | Deportes Melipilla | 0:1 | ||||
| 22. Ronde | 08.09.2019 | Puerto Montt | - | Cobreloa | 1:1 |
Chili