| 14. Round | 25/05/2019 | Deportes Melipilla | - | Puerto Montt | 2:0 | ||||
| 15. Round | 02/06/2019 | Deportes Valdivia | - | Deportes Melipilla | 1:1 | ||||
| 16. Round | 30/07/2019 | Deportes Melipilla | - | Santiago Wanderers | 2:1 | ||||
| 17. Round | 03/08/2019 | Barnechea | - | Deportes Melipilla | 0:1 | ||||
| 18. Round | 11/08/2019 | Deportes Melipilla | - | Ñublense | 1:1 |  |
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| 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 | |
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| 24. Round | 29/09/2019 | Deportes Melipilla | - | Santa Cruz | 2:2 | ||||
| 25. Round | 06/10/2019 | Deportes Melipilla | - | Unión San Felipe | 0:2 | ||||
| 26. Round | 12/10/2019 | Puerto Montt | - | Deportes Melipilla | 1:3 |
Chile