2. Round | 19/08/2019 | FC Utrecht (J) | - | TOP Oss | 2:1 | ||||
3. Round | 23/08/2019 | TOP Oss | - | AZ Alkmaar (J) | 1:2 | ||||
4. Round | 30/08/2019 | TOP Oss | - | De Graafschap | 0:0 | ||||
5. Round | 08/09/2019 | Roda JC Kerkrade | - | TOP Oss | 2:1 | ||||
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 | ||||
11. Round | 18/10/2019 | SC Cambuur | - | TOP Oss | 5:1 | ||||
12. Round | 25/10/2019 | TOP Oss | - | Jong PSV | 1:0 | ||||
13. Round | 01/11/2019 | FC Dordrecht | - | TOP Oss | 1:1 | ||||
14. Round | 08/11/2019 | NEC Nijmegen | - | TOP Oss | 3:0 | ||||
15. Round | 15/11/2019 | TOP Oss | - | FC Volendam | 1:2 | ||||
20. Round | 20/12/2019 | Jong Ajax | - | TOP Oss | 2:0 | ||||
23. Round | 24/01/2020 | Telstar | - | TOP Oss | 1:0 | ||||
27. Round | 21/02/2020 | Jong PSV | - | TOP Oss | 1:1 |