| 6. Round | 23/09/2023 | FC Volendam | - | Heracles Almelo | 2:2 | ||||
| 3. Round | 28/09/2023 | AZ Alkmaar | - | Heracles Almelo | 1:1 | ||||
| 11. Round | 04/11/2023 | Heracles Almelo | - | PSV Eindhoven | 0:6 | ||||
| 12. Round | 10/11/2023 | Fortuna Sittard | - | Heracles Almelo | 4:1 | ||||
| 17. Round | 12/01/2024 | RKC Waalwijk | - | Heracles Almelo | 1:2 | ||||
| 19. Round | 27/01/2024 | Heracles Almelo | - | AFC Ajax | 2:4 |  |
Germany