| 1. Round | 04/08/2019 | Union Saint-Gilloise | - | KSV Roeselare | 3:0 | ||||
| 2. Round | 10/08/2019 | KSV Roeselare | - | K Beerschot VA | 1:1 | ||||
| 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 | ||||
| 9. Round | 04/10/2019 | Lommel SK | - | KSV Roeselare | 2:1 |  |
|||
| 11. Round | 19/10/2019 | KSV Roeselare | - | Union Saint-Gilloise | 3:0 | ||||
| 14. Round | 08/11/2019 | KSV Roeselare | - | Sporting Lokeren | 2:1 |
Belgium
Uruguay