| 14. Jornada | 25.05.2019 | Deportes Melipilla | - | Puerto Montt | 2:0 | ||||
| 15. Jornada | 02.06.2019 | Deportes Valdivia | - | Deportes Melipilla | 1:1 | ||||
| 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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| 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 | |
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| 24. Jornada | 29.09.2019 | Deportes Melipilla | - | Santa Cruz | 2:2 | ||||
| 25. Jornada | 06.10.2019 | Deportes Melipilla | - | Unión San Felipe | 0:2 | ||||
| 26. Jornada | 12.10.2019 | Puerto Montt | - | Deportes Melipilla | 1:3 |
Chile