| 1. Round | 16/02/2019 | Puerto Montt | - | Ñublense | 2:2 | ||||
| 3. Round | 02/03/2019 | Puerto Montt | - | Santa Cruz | 0:0 | ||||
| 4. Round | 09/03/2019 | CD Magallanes | - | Puerto Montt | 1:1 | ||||
| 5. Round | 16/03/2019 | Puerto Montt | - | La Serena | 1:0 | ||||
| 6. Round | 31/03/2019 | Puerto Montt | - | Santiago Morning | 2:1 | ||||
| 7. Round | 07/04/2019 | Cobreloa | - | Puerto Montt | 2:1 | ||||
| 11. Round | 04/05/2019 | Puerto Montt | - | Deportes Copiapó | 2:2 | ||||
| 12. Round | 12/05/2019 | Deportes Valdivia | - | Puerto Montt | 0:5 | ||||
| 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 | ||||
| 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 | ||||
| 23. Round | 15/09/2019 | Deportes Temuco | - | Puerto Montt | 0:1 | |
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| 24. Round | 28/09/2019 | Puerto Montt | - | CD Magallanes | 1:1 | ||||
| 27. Round | 19/10/2019 | Ñublense | - | Puerto Montt | 2:0 |
Chile