| 2. Round | 28/07/2019 | Real Cartagena | - | Valledupar FC | 2:2 | ||||
| 4. Round | 11/08/2019 | Real San Andrés | - | Valledupar FC | 2:1 | ||||
| 5. Round | 17/08/2019 | Valledupar FC | - | Orsomarso SC | 3:1 | ||||
| 7. Round | 26/08/2019 | Tigres FC | - | Valledupar FC | 1:2 |  |
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| 8. Round | 01/09/2019 | Atlético FC | - | Valledupar FC | 0:0 | |
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| 9. Round | 08/09/2019 | Deportes Quindío | - | Valledupar FC | 0:0 | ||||
| 11. Round | 18/09/2019 | Fortaleza FC | - | Valledupar FC | 0:0 | ||||
| 13. Round | 30/09/2019 | Boyacá Chicó | - | Valledupar FC | 1:0 |
Colombia