4. Round | 30/08/2019 | TOP Oss | - | De Graafschap | 0:0 | ||||
6. Round | 14/09/2019 | TOP Oss | - | Go Ahead Eagles | 1:2 | ||||
7. Round | 21/09/2019 | Helmond Sport | - | TOP Oss | 0:2 | ||||
8. Round | 27/09/2019 | TOP Oss | - | NAC Breda | 0:1 | ||||
9. Round | 04/10/2019 | FC Den Bosch | - | TOP Oss | 4:0 | ||||
10. Round | 12/10/2019 | TOP Oss | - | Telstar | 2:2 | ||||
12. Round | 25/10/2019 | TOP Oss | - | Jong PSV | 1:0 |