| 16. Round | 27/07/2019 | Puerto Montt | - | Deportes Valdivia | 4:1 | ||||
| 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 | ||||
| 22. Round | 08/09/2019 | Puerto Montt | - | Cobreloa | 1:1 | ||||
| 25. Round | 05/10/2019 | Santa Cruz | - | Puerto Montt | 2:0 | ||||
| 26. Round | 12/10/2019 | Puerto Montt | - | Melipilla | 1:3 | ||||
| 27. Round | 19/10/2019 | Ñublense | - | Puerto Montt | 2:0 |
Chile