| 1. Ronde | 11.08.2023 | Roda JC Kerkrade | - | Helmond Sport | 4:1 |  |
|||
| 2. Ronde | 18.08.2023 | Helmond Sport | - | FC Den Bosch | 1:0 | ||||
| 3. Ronde | 28.08.2023 | Jong PSV | - | Helmond Sport | 2:1 | ||||
| 4. Ronde | 01.09.2023 | Helmond Sport | - | SC Cambuur | 2:1 | |
 |
||
| 6. Ronde | 15.09.2023 | Helmond Sport | - | TOP Oss | 1:1 | ||||
| 5. Ronde | 18.09.2023 | De Graafschap | - | Helmond Sport | 2:1 | |
|||
| 7. Ronde | 22.09.2023 | Helmond Sport | - | FC Groningen | 1:2 | |
|||
| 8. Ronde | 01.10.2023 | VVV-Venlo | - | Helmond Sport | 0:4 | |
|||
| 9. Ronde | 06.10.2023 | Helmond Sport | - | Jong FC Utrecht | 4:0 | |
|||
| 11. Ronde | 20.10.2023 | FC Eindhoven | - | Helmond Sport | 1:2 | |
|||
| 10. Ronde | 23.10.2023 | Helmond Sport | - | FC Dordrecht | 1:1 | ||||
| 12. Ronde | 27.10.2023 | NAC Breda | - | Helmond Sport | 1:1 | |
|||
| 13. Ronde | 03.11.2023 | Helmond Sport | - | Telstar | 1:0 | |
|||
| 14. Ronde | 10.11.2023 | Jong AZ Alkmaar | - | Helmond Sport | 2:1 | |
|||
| 16. Ronde | 24.11.2023 | Helmond Sport | - | FC Emmen | 1:2 | |
|||
| 15. Ronde | 27.11.2023 | Jong Ajax | - | Helmond Sport | 4:1 | ||||
| 17. Ronde | 01.12.2023 | Helmond Sport | - | ADO Den Haag | 3:2 | |
Nederland