| 1. Round | 11/08/2023 | FC Den Bosch | - | TOP Oss | 1:0 | ||||
| 2. Round | 18/08/2023 | TOP Oss | - | Jong PSV | 4:1 | ||||
| 3. Round | 25/08/2023 | Roda JC Kerkrade | - | TOP Oss | 2:0 | ||||
| 4. Round | 01/09/2023 | TOP Oss | - | FC Groningen | 0:2 | ||||
| 10. Round | 23/10/2023 | TOP Oss | - | FC Utrecht (J) | 2:0 |  |
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| 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 | ||||
| 17. Round | 01/12/2023 | TOP Oss | - | De Graafschap | 0:1 | ||||
| 18. Round | 08/12/2023 | NAC Breda | - | TOP Oss | 2:0 | ||||
| 24. Round | 02/02/2024 | TOP Oss | - | ADO Den Haag | 1:3 | ||||
| 36. Round | 26/04/2024 | TOP Oss | - | AZ Alkmaar (J) | 1:1 |
Netherlands