| 10. Round | 28/04/2019 | Deportes Melipilla | - | La Serena | 4:0 | ||||
| 11. Round | 04/05/2019 | Santiago Wanderers | - | Deportes Melipilla | 2:1 |  |
|||
| 12. Round | 11/05/2019 | Deportes Melipilla | - | Barnechea | 0:0 | ||||
| 13. Round | 18/05/2019 | Santa Cruz | - | Deportes Melipilla | 1:0 | ||||
| 21. Round | 31/08/2019 | Cobreloa | - | Deportes Melipilla | 0:1 | ||||
| 22. Round | 08/09/2019 | Deportes Melipilla | - | Deportes Valdivia | 2:0 | ||||
| 23. Round | 14/09/2019 | CD Magallanes | - | Deportes Melipilla | 1:2 | ||||
| 26. Round | 12/10/2019 | Puerto Montt | - | Deportes Melipilla | 1:3 |
Chile