1. Round | 11/08/2023 | Roda JC Kerkrade | - | Helmond Sport | 4:1 | ||||
3. Round | 28/08/2023 | Jong PSV | - | Helmond Sport | 2:1 | ||||
4. Round | 01/09/2023 | Helmond Sport | - | SC Cambuur | 2:1 | ||||
6. Round | 15/09/2023 | Helmond Sport | - | TOP Oss | 1:1 | ||||
5. Round | 18/09/2023 | De Graafschap | - | Helmond Sport | 2:1 | ||||
8. Round | 01/10/2023 | VVV-Venlo | - | Helmond Sport | 0:4 | ||||
11. Round | 20/10/2023 | FC Eindhoven | - | Helmond Sport | 1:2 | ||||
16. Round | 24/11/2023 | Helmond Sport | - | FC Emmen | 1:2 |