| 1. Round | 16/02/2019 | Puerto Montt | - | Ñublense | 2:2 | ||||
| 2. Round | 22/02/2019 | Barnechea | - | Puerto Montt | 2:1 | ||||
| 3. Round | 02/03/2019 | Puerto Montt | - | Santa Cruz | 0:0 | ||||
| 4. Round | 09/03/2019 | CD Magallanes | - | Puerto Montt | 1:1 |  |
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| 5. Round | 16/03/2019 | Puerto Montt | - | La Serena | 1:0 | ||||
| 8. Round | 13/04/2019 | Rangers | - | Puerto Montt | 0:3 | ||||
| 9. Round | 20/04/2019 | Puerto Montt | - | Unión San Felipe | 0:0 | ||||
| 10. Round | 28/04/2019 | San Luis | - | Puerto Montt | 1:1 | ||||
| 11. Round | 04/05/2019 | Puerto Montt | - | Deportes Copiapó | 2:2 | ||||
| 12. Round | 12/05/2019 | Deportes Valdivia | - | Puerto Montt | 0:5 | |
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| 13. Round | 18/05/2019 | Puerto Montt | - | Deportes Temuco | 2:1 | ||||
| 14. Round | 25/05/2019 | Deportes Melipilla | - | Puerto Montt | 2:0 |
Chile