| 16. Round | 27/07/2019 | Puerto Montt | - | Deportes Valdivia | 4:1 |  |
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| 17. Round | 05/08/2019 | Santiago Morning | - | Puerto Montt | 1:0 | ||||
| 18. Round | 10/08/2019 | Puerto Montt | - | Barnechea | 3:0 | |
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| 19. Round | 17/08/2019 | Santiago Wanderers | - | Puerto Montt | 1:1 | ||||
| 20. Round | 24/08/2019 | Puerto Montt | - | Rangers | 0:0 | ||||
| 21. Round | 31/08/2019 | Unión San Felipe | - | Puerto Montt | 2:1 | ||||
| 22. Round | 08/09/2019 | Puerto Montt | - | Cobreloa | 1:1 | ||||
| 23. Round | 15/09/2019 | Deportes Temuco | - | Puerto Montt | 0:1 | ||||
| 24. Round | 28/09/2019 | Puerto Montt | - | CD Magallanes | 1:1 |  |
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| 25. Round | 05/10/2019 | Santa Cruz | - | Puerto Montt | 2:0 | |
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| 26. Round | 12/10/2019 | Puerto Montt | - | Deportes Melipilla | 1:3 | ||||
| 27. Round | 19/10/2019 | Ñublense | - | Puerto Montt | 2:0 |
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