| 1. Round | 16/02/2019 | Santiago Morning | - | Deportes Melipilla | 3:2 |  |
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| 2. Round | 23/02/2019 | Deportes Melipilla | - | Cobreloa | 1:1 |  |
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| 3. Round | 03/03/2019 | Deportes Copiapó | - | Deportes Melipilla | 1:3 | ||||
| 4. Round | 09/03/2019 | Deportes Melipilla | - | San Luis | 1:1 | ||||
| 5. Round | 16/03/2019 | Deportes Melipilla | - | Rangers | 0:0 | ||||
| 6. Round | 30/03/2019 | Deportes Temuco | - | Deportes Melipilla | 1:1 | |
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| 9. Round | 21/04/2019 | Ñublense | - | Deportes Melipilla | 2:0 | ||||
| 11. Round | 04/05/2019 | Santiago Wanderers | - | Deportes Melipilla | 2:1 | ||||
| 13. Round | 18/05/2019 | Santa Cruz | - | Deportes Melipilla | 1:0 | ||||
| 18. Round | 11/08/2019 | Deportes Melipilla | - | Ñublense | 1:1 |
Chile