| 3. Round | 25/08/2023 | Roda JC Kerkrade | - | TOP Oss | 2:0 | ||||
| 4. Round | 01/09/2023 | TOP Oss | - | FC Groningen | 0:2 | ||||
| 6. Round | 15/09/2023 | Helmond Sport | - | TOP Oss | 1:1 |  |
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| 5. Round | 18/09/2023 | TOP Oss | - | FC Dordrecht | 0:1 | ||||
| 8. Round | 29/09/2023 | TOP Oss | - | FC Emmen | 0:1 | ||||
| 7. Round | 03/10/2023 | Willem II | - | TOP Oss | 2:1 | ||||
| 9. Round | 06/10/2023 | ADO Den Haag | - | TOP Oss | 2:1 | ||||
| 11. Round | 20/10/2023 | AZ Alkmaar (J) | - | TOP Oss | 3:0 | ||||
| 28. Round | 01/03/2024 | De Graafschap | - | TOP Oss | 2:1 | ||||
| 29. Round | 08/03/2024 | TOP Oss | - | FC Den Bosch | 1:2 | ||||
| 31. Round | 11/03/2024 | FC Emmen | - | TOP Oss | 0:1 | |
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| 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 | ||||
| 35. Round | 19/04/2024 | FC Dordrecht | - | TOP Oss | 3:1 | ||||
| 36. Round | 26/04/2024 | TOP Oss | - | AZ Alkmaar (J) | 1:1 | ||||
| 37. Round | 03/05/2024 | Jong PSV | - | TOP Oss | 4:1 | ||||
| 38. Round | 10/05/2024 | TOP Oss | - | NAC Breda | 1:1 |
Netherlands