| 2. Jornada | 23.02.2019 | Deportes Melipilla | - | Cobreloa | 1:1 | ||||
| 8. Jornada | 13.04.2019 | Unión San Felipe | - | Deportes Melipilla | 2:0 | ||||
| 9. Jornada | 21.04.2019 | Ñublense | - | Deportes Melipilla | 2:0 | ||||
| 11. Jornada | 04.05.2019 | Santiago Wanderers | - | Deportes Melipilla | 2:1 | ||||
| 12. Jornada | 11.05.2019 | Deportes Melipilla | - | Barnechea | 0:0 | ||||
| 16. Jornada | 30.07.2019 | Deportes Melipilla | - | Santiago Wanderers | 2:1 | ||||
| 17. Jornada | 03.08.2019 | Barnechea | - | Deportes Melipilla | 0:1 | ||||
| 18. Jornada | 11.08.2019 | Deportes Melipilla | - | Ñublense | 1:1 |  |
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| 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 | ||||
| 24. Jornada | 29.09.2019 | Deportes Melipilla | - | Santa Cruz | 2:2 | ||||
| 26. Jornada | 12.10.2019 | Puerto Montt | - | Deportes Melipilla | 1:3 |
Chile