| 1. Jornada | 16.02.2019 | Santiago Morning | - | Deportes Melipilla | 3:2 |  |
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| 10. Jornada | 28.04.2019 | Deportes Melipilla | - | La Serena | 4:0 | ||||
| 12. Jornada | 11.05.2019 | Deportes Melipilla | - | Barnechea | 0:0 |  |
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| 13. Jornada | 19.05.2019 | Santa Cruz | - | Deportes Melipilla | 1:0 | ||||
| 14. Jornada | 25.05.2019 | Deportes Melipilla | - | Puerto Montt | 2:0 | ||||
| 16. Jornada | 30.07.2019 | Deportes Melipilla | - | Santiago Wanderers | 2:1 | |
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| 17. Jornada | 03.08.2019 | Barnechea | - | Deportes Melipilla | 0:1 | ||||
| 18. Jornada | 11.08.2019 | Deportes Melipilla | - | Ñublense | 1:1 | ||||
| 19. Jornada | 18.08.2019 | Rangers | - | Deportes Melipilla | 2:0 | ||||
| 20. Jornada | 24.08.2019 | Deportes Melipilla | - | Santiago Morning | 3:1 | ||||
| 21. Jornada | 31.08.2019 | Cobreloa | - | Deportes Melipilla | 0:1 | ||||
| 22. Jornada | 08.09.2019 | Deportes Melipilla | - | Deportes Valdivia | 2:0 | ||||
| 23. Jornada | 14.09.2019 | CD Magallanes | - | Deportes Melipilla | 1:2 | |
Chile