| 5. Round | 05/09/2022 | Jong Ajax | - | Heracles Almelo | 4:0 | ||||
| 7. Round | 16/09/2022 | Telstar | - | Heracles Almelo | 0:3 | ||||
| 10. Round | 07/10/2022 | Heracles Almelo | - | De Graafschap | 3:2 | ||||
| 11. Round | 14/10/2022 | PEC Zwolle | - | Heracles Almelo | 3:2 | ||||
| 12. Round | 21/10/2022 | Heracles Almelo | - | FC Eindhoven | 3:0 |  |
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| 13. Round | 28/10/2022 | Almere City FC | - | Heracles Almelo | 3:2 |  |
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| 16. Round | 19/11/2022 | Heracles Almelo | - | TOP Oss | 3:0 | |
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| 17. Round | 11/12/2022 | Roda JC Kerkrade | - | Heracles Almelo | 1:3 | ||||
| 22. Round | 27/01/2023 | FC Eindhoven | - | Heracles Almelo | 1:0 | ||||
| 24. Round | 10/02/2023 | VVV-Venlo | - | Heracles Almelo | 3:1 | ||||
| 21. Round | 13/02/2023 | MVV | - | Heracles Almelo | 0:2 | ||||
| 25. Round | 17/02/2023 | Heracles Almelo | - | Willem II | 1:1 | ||||
| 31. Round | 31/03/2023 | Heracles Almelo | - | Almere City FC | 1:1 | ||||
| 32. Round | 07/04/2023 | De Graafschap | - | Heracles Almelo | 5:3 | |
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| 35. Round | 28/04/2023 | Heracles Almelo | - | Jong PSV | 3:0 | ||||
| 36. Round | 05/05/2023 | FC Dordrecht | - | Heracles Almelo | 1:3 | ||||
| 37. Round | 12/05/2023 | NAC Breda | - | Heracles Almelo | 0:3 |
Croatia