| 1. Round | 29/08/2020 | TOP Oss | - | Helmond Sport | 1:2 | ||||
| 2. Round | 05/09/2020 | Roda JC Kerkrade | - | TOP Oss | 3:0 | ||||
| 4. Round | 19/09/2020 | TOP Oss | - | SC Cambuur | 2:2 | ||||
| 6. Round | 05/10/2020 | TOP Oss | - | FC Dordrecht | 2:0 | ||||
| 15. Round | 05/12/2020 | AZ Alkmaar (J) | - | TOP Oss | 0:1 | ||||
| 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 | ||||
| 19. Round | 10/01/2021 | Go Ahead Eagles | - | TOP Oss | 1:0 | ||||
| 20. Round | 16/01/2021 | TOP Oss | - | Telstar | 1:4 | ||||
| 21. Round | 23/01/2021 | TOP Oss | - | SBV Excelsior | 1:3 | ||||
| 22. Round | 29/01/2021 | De Graafschap | - | TOP Oss | 2:1 | ||||
| 30. Round | 26/03/2021 | FC Eindhoven | - | TOP Oss | 0:0 | ||||
| 31. Round | 02/04/2021 | FC Den Bosch | - | TOP Oss | 1:0 | ||||
| 32. Round | 05/04/2021 | TOP Oss | - | FC Volendam | 2:0 | ||||
| 33. Round | 09/04/2021 | Jong Ajax | - | TOP Oss | 0:1 | ||||
| 34. Round | 16/04/2021 | TOP Oss | - | MVV | 2:2 | ||||
| 37. Round | 07/05/2021 | Helmond Sport | - | TOP Oss | 1:1 | ||||
| 38. Round | 12/05/2021 | TOP Oss | - | Roda JC Kerkrade | 2:0 |
Netherlands