| 1. Jornada | 04.08.2019 | Union Saint-Gilloise | - | KSV Roeselare | 3:0 | ||||
| 2. Jornada | 10.08.2019 | KSV Roeselare | - | K Beerschot VA | 1:1 | ||||
| 3. Jornada | 17.08.2019 | KVC Westerlo | - | KSV Roeselare | 4:1 |  |
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| 10. Jornada | 12.10.2019 | KSV Roeselare | - | Oud-Heverlee Leuven | 3:1 | ||||
| 11. Jornada | 19.10.2019 | KSV Roeselare | - | Union Saint-Gilloise | 3:0 | ||||
| 12. Jornada | 27.10.2019 | Excelsior Virton | - | KSV Roeselare | 3:2 | ||||
| 13. Jornada | 02.11.2019 | K Beerschot VA | - | KSV Roeselare | 2:1 | ||||
| 14. Jornada | 08.11.2019 | KSV Roeselare | - | Sporting Lokeren | 2:1 |  |
Bélgica