| 1. Round | 05/08/2022 | NAC Breda | - | Helmond Sport | 1:0 | ||||
| 2. Round | 12/08/2022 | Helmond Sport | - | AZ Alkmaar (J) | 1:3 |  |
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| 3. Round | 19/08/2022 | Helmond Sport | - | FC Eindhoven | 0:1 | ||||
| 5. Round | 02/09/2022 | Helmond Sport | - | Almere City FC | 3:0 | ||||
| 12. Round | 24/10/2022 | Jong PSV | - | Helmond Sport | 6:0 | |
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| 16. Round | 18/11/2022 | Helmond Sport | - | De Graafschap | 0:2 | ||||
| 18. Round | 16/12/2022 | Helmond Sport | - | FC Den Bosch | 1:0 | ||||
| 19. Round | 06/01/2023 | VVV-Venlo | - | Helmond Sport | 1:1 | |
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| 20. Round | 13/01/2023 | Helmond Sport | - | NAC Breda | 2:2 | ||||
| 21. Round | 23/01/2023 | AZ Alkmaar (J) | - | Helmond Sport | 1:1 | ||||
| 22. Round | 27/01/2023 | Helmond Sport | - | Jong Ajax | 1:1 | ||||
| 23. Round | 03/02/2023 | Willem II | - | Helmond Sport | 5:1 | |
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| 33. Round | 14/04/2023 | FC Den Bosch | - | Helmond Sport | 1:2 | ||||
| 34. Round | 21/04/2023 | Helmond Sport | - | Heracles Almelo | 0:1 | ||||
| 35. Round | 28/04/2023 | ADO Den Haag | - | Helmond Sport | 2:2 | ||||
| 36. Round | 05/05/2023 | Helmond Sport | - | VVV-Venlo | 1:1 | ||||
| 37. Round | 12/05/2023 | FC Eindhoven | - | Helmond Sport | 0:1 | ||||
| 38. Round | 19/05/2023 | Helmond Sport | - | PEC Zwolle | 2:3 |
Belgium