| 1. Round | 04/08/2019 | Union Saint-Gilloise | - | KSV Roeselare | 3:0 | ||||
| 2. Round | 10/08/2019 | KSV Roeselare | - | K Beerschot VA | 1:1 |  |
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| 3. Round | 17/08/2019 | KVC Westerlo | - | KSV Roeselare | 4:1 | ||||
| 4. Round | 31/08/2019 | KSV Roeselare | - | Lommel SK | 1:1 | ||||
| 5. Round | 07/09/2019 | Oud-Heverlee Leuven | - | KSV Roeselare | 4:0 | ||||
| 7. Round | 20/09/2019 | Sporting Lokeren | - | KSV Roeselare | 2:0 | ||||
| 8. Round | 27/09/2019 | KSV Roeselare | - | KVC Westerlo | 0:2 | ||||
| 9. Round | 04/10/2019 | Lommel SK | - | KSV Roeselare | 2:1 | ||||
| 11. Round | 19/10/2019 | KSV Roeselare | - | Union Saint-Gilloise | 3:0 | |
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| 12. Round | 27/10/2019 | Excelsior Virton | - | KSV Roeselare | 3:2 | ||||
| 13. Round | 02/11/2019 | K Beerschot VA | - | KSV Roeselare | 2:1 | |
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| 14. Round | 08/11/2019 | KSV Roeselare | - | Sporting Lokeren | 2:1 | |
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