| 1. Round | 16/02/2019 | Santiago Morning | - | Deportes Melipilla | 3:2 |  |
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| 10. Round | 28/04/2019 | Deportes Melipilla | - | La Serena | 4:0 | ||||
| 12. Round | 11/05/2019 | Deportes Melipilla | - | Barnechea | 0:0 |  |
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| 13. Round | 18/05/2019 | Santa Cruz | - | Deportes Melipilla | 1:0 | ||||
| 14. Round | 25/05/2019 | Deportes Melipilla | - | Puerto Montt | 2:0 | ||||
| 16. Round | 30/07/2019 | Deportes Melipilla | - | Santiago Wanderers | 2:1 | |
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| 17. Round | 03/08/2019 | Barnechea | - | Deportes Melipilla | 0:1 | ||||
| 18. Round | 11/08/2019 | Deportes Melipilla | - | Ñublense | 1:1 | ||||
| 19. Round | 18/08/2019 | Rangers | - | Deportes Melipilla | 2:0 | ||||
| 20. Round | 24/08/2019 | Deportes Melipilla | - | Santiago Morning | 3:1 | ||||
| 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 | |
Chile