| 2. Round | 05/09/2020 | Roda JC Kerkrade | - | TOP Oss | 3:0 | ||||
| 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 | ||||
| 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 | ||||
| 23. Round | 05/02/2021 | TOP Oss | - | AZ Alkmaar (J) | 6:0 |  |
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| 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 |  |
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| 34. Round | 16/04/2021 | TOP Oss | - | MVV | 2:2 | ||||
| 36. Round | 30/04/2021 | TOP Oss | - | FC Utrecht (J) | 0:4 | ||||
| 35. Round | 03/05/2021 | Jong PSV | - | TOP Oss | 0:0 | ||||
| 37. Round | 07/05/2021 | Helmond Sport | - | TOP Oss | 1:1 | ||||
| 38. Round | 12/05/2021 | TOP Oss | - | Roda JC Kerkrade | 2:0 |
Netherlands