| 1. Round | 29/08/2020 | TOP Oss | - | Helmond Sport | 1:2 | ||||
| 2. Round | 05/09/2020 | Roda JC Kerkrade | - | TOP Oss | 3:0 | ||||
| 3. Round | 15/09/2020 | Almere City FC | - | TOP Oss | 3:0 | ||||
| 5. Round | 25/09/2020 | MVV | - | TOP Oss | 3:0 | ||||
| 6. Round | 05/10/2020 | TOP Oss | - | FC Dordrecht | 2:0 | ||||
| 7. Round | 10/10/2020 | Telstar | - | TOP Oss | 1:1 | ||||
| 8. Round | 20/10/2020 | TOP Oss | - | FC Den Bosch | 2:0 | ||||
| 10. Round | 30/10/2020 | TOP Oss | - | De Graafschap | 0:2 | ||||
| 11. Round | 10/11/2020 | SBV Excelsior | - | TOP Oss | 3:0 | ||||
| 12. Round | 13/11/2020 | TOP Oss | - | FC Eindhoven | 0:1 | ||||
| 13. Round | 20/11/2020 | FC Volendam | - | TOP Oss | 1:1 | ||||
| 14. Round | 27/11/2020 | TOP Oss | - | NAC Breda | 0:0 | ||||
| 15. Round | 05/12/2020 | AZ Alkmaar (J) | - | TOP Oss | 0:1 | ||||
| 16. Round | 11/12/2020 | TOP Oss | - | Jong PSV | 3:2 | ||||
| 9. Round | 14/12/2020 | FC Utrecht (J) | - | TOP Oss | 0:1 | ||||
| 17. Round | 19/12/2020 | NEC Nijmegen | - | TOP Oss | 0:1 | ||||
| 18. Round | 05/01/2021 | TOP Oss | - | Jong Ajax | 1:0 |  |
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| 19. Round | 10/01/2021 | Go Ahead Eagles | - | TOP Oss | 1:0 | ||||
| 36. Round | 30/04/2021 | TOP Oss | - | FC Utrecht (J) | 0:4 | ||||
| 37. Round | 07/05/2021 | Helmond Sport | - | TOP Oss | 1:1 | ||||
| 38. Round | 12/05/2021 | TOP Oss | - | Roda JC Kerkrade | 2:0 |
Netherlands