| 16. Jornada | 27.07.2019 | Puerto Montt | - | Deportes Valdivia | 4:1 |  |
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| 17. Jornada | 05.08.2019 | Santiago Morning | - | Puerto Montt | 1:0 | ||||
| 18. Jornada | 10.08.2019 | Puerto Montt | - | Barnechea | 3:0 | |
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| 19. Jornada | 17.08.2019 | Santiago Wanderers | - | Puerto Montt | 1:1 | ||||
| 20. Jornada | 24.08.2019 | Puerto Montt | - | Rangers | 0:0 | ||||
| 21. Jornada | 31.08.2019 | Unión San Felipe | - | Puerto Montt | 2:1 | ||||
| 22. Jornada | 08.09.2019 | Puerto Montt | - | Cobreloa | 1:1 | ||||
| 23. Jornada | 15.09.2019 | Deportes Temuco | - | Puerto Montt | 0:1 | ||||
| 24. Jornada | 28.09.2019 | Puerto Montt | - | CD Magallanes | 1:1 |  |
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| 25. Jornada | 06.10.2019 | Santa Cruz | - | Puerto Montt | 2:0 | |
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| 26. Jornada | 12.10.2019 | Puerto Montt | - | Deportes Melipilla | 1:3 | ||||
| 27. Jornada | 19.10.2019 | Ñublense | - | Puerto Montt | 2:0 |
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