1. Round | 11/08/2023 | Roda JC Kerkrade | - | Helmond Sport | 4:1 | ||||
2. Round | 18/08/2023 | Helmond Sport | - | FC Den Bosch | 1:0 | ||||
3. Round | 28/08/2023 | Jong PSV | - | Helmond Sport | 2:1 | ||||
6. Round | 15/09/2023 | Helmond Sport | - | TOP Oss | 1:1 | ||||
7. Round | 22/09/2023 | Helmond Sport | - | FC Groningen | 1:2 | ||||
8. Round | 01/10/2023 | VVV-Venlo | - | Helmond Sport | 0:4 | ||||
9. Round | 06/10/2023 | Helmond Sport | - | FC Utrecht (J) | 4:0 | ||||
11. Round | 20/10/2023 | FC Eindhoven | - | Helmond Sport | 1:2 | ||||
12. Round | 27/10/2023 | NAC Breda | - | Helmond Sport | 1:1 | ||||
13. Round | 03/11/2023 | Helmond Sport | - | Telstar | 1:0 | ||||
19. Round | 15/12/2023 | Willem II | - | Helmond Sport | 4:1 | ||||
21. Round | 12/01/2024 | FC Dordrecht | - | Helmond Sport | 2:0 | ||||
25. Round | 09/02/2024 | Telstar | - | Helmond Sport | 3:2 | ||||
26. Round | 16/02/2024 | Helmond Sport | - | De Graafschap | 3:1 | ||||
27. Round | 23/02/2024 | FC Groningen | - | Helmond Sport | 0:0 | ||||
29. Round | 08/03/2024 | FC Utrecht (J) | - | Helmond Sport | 0:1 | ||||
31. Round | 11/03/2024 | Helmond Sport | - | AZ Alkmaar (J) | 3:1 | ||||
35. Round | 19/04/2024 | Helmond Sport | - | Jong Ajax | 3:1 |