| 15. Round | 02/06/2019 | Deportes Valdivia | - | Deportes Melipilla | 1:1 | ||||
| 17. Round | 04/08/2019 | Deportes Valdivia | - | Deportes Copiapó | 1:1 |  |
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| 18. Round | 13/08/2019 | La Serena | - | Deportes Valdivia | 2:1 | ||||
| 20. Round | 26/08/2019 | San Luis | - | Deportes Valdivia | 1:1 | ||||
| 23. Round | 16/09/2019 | Deportes Valdivia | - | Santiago Morning | 1:2 |  |
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| 25. Round | 06/10/2019 | Cobreloa | - | Deportes Valdivia | 2:1 | ||||
| 26. Round | 13/10/2019 | Deportes Valdivia | - | Ñublense | 2:3 | |
Chile