| 1. Round | 16/02/2019 | Santiago Morning | - | Deportes Melipilla | 3:2 | ||||
| 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 |  |
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| 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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| 7. Round | 07/04/2019 | Deportes Melipilla | - | CD Magallanes | 0:0 | |
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| 8. Round | 13/04/2019 | Unión San Felipe | - | Deportes Melipilla | 2:0 | |
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| 9. Round | 21/04/2019 | Ñublense | - | Deportes Melipilla | 2:0 | ||||
| 10. Round | 28/04/2019 | Deportes Melipilla | - | La Serena | 4:0 | |
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| 11. Round | 04/05/2019 | Santiago Wanderers | - | Deportes Melipilla | 2:1 | |
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| 13. Round | 18/05/2019 | Santa Cruz | - | Deportes Melipilla | 1:0 | |
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| 14. Round | 25/05/2019 | Deportes Melipilla | - | Puerto Montt | 2:0 |
Chile