| 1. Round | 11/08/2023 | FC Den Bosch | - | TOP Oss | 1:0 |  |
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| 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 | ||||
| 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 | ||||
| 7. Round | 03/10/2023 | Willem II | - | TOP Oss | 2:1 | ||||
| 16. Round | 24/11/2023 | Jong Ajax | - | TOP Oss | 1:0 | ||||
| 15. Round | 27/11/2023 | FC Eindhoven | - | TOP Oss | 0:0 |
Greece