| 11. Round | 20/10/2023 | AZ Alkmaar (J) | - | TOP Oss | 3:0 | ||||
| 10. Round | 23/10/2023 | TOP Oss | - | FC Utrecht (J) | 2:0 | ||||
| 12. Round | 27/10/2023 | Telstar | - | TOP Oss | 1:0 | ||||
| 13. Round | 06/11/2023 | TOP Oss | - | SC Cambuur | 1:8 | ||||
| 14. Round | 10/11/2023 | TOP Oss | - | MVV | 0:1 | ||||
| 16. Round | 24/11/2023 | Jong Ajax | - | TOP Oss | 1:0 | ||||
| 15. Round | 27/11/2023 | FC Eindhoven | - | TOP Oss | 0:0 | ||||
| 20. Round | 22/12/2023 | MVV | - | TOP Oss | 2:0 | ||||
| 22. Round | 19/01/2024 | TOP Oss | - | Telstar | 1:0 | ||||
| 23. Round | 29/01/2024 | SC Cambuur | - | TOP Oss | 1:2 | ||||
| 25. Round | 11/02/2024 | FC Groningen | - | TOP Oss | 3:0 | ||||
| 29. Round | 08/03/2024 | TOP Oss | - | FC Den Bosch | 1:2 | ||||
| 31. Round | 11/03/2024 | FC Emmen | - | TOP Oss | 0:1 | ||||
| 30. Round | 15/03/2024 | TOP Oss | - | Helmond Sport | 1:0 |  |
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| 32. Round | 29/03/2024 | VVV-Venlo | - | TOP Oss | 2:0 | ||||
| 33. Round | 05/04/2024 | TOP Oss | - | FC Eindhoven | 2:1 | ||||
| 34. Round | 12/04/2024 | TOP Oss | - | Roda JC Kerkrade | 1:4 | ||||
| 37. Round | 03/05/2024 | Jong PSV | - | TOP Oss | 4:1 | ||||
| 38. Round | 10/05/2024 | TOP Oss | - | NAC Breda | 1:1 |
Netherlands