| 6. Round | 01/09/2018 | Accrington Stanley | - | Scunthorpe United | 1:1 | ||||
| 7. Round | 08/09/2018 | Scunthorpe United | - | Rochdale AFC | 3:3 | ||||
| 8. Round | 15/09/2018 | AFC Wimbledon | - | Scunthorpe United | 2:3 |  |
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| 9. Round | 22/09/2018 | Scunthorpe United | - | Shrewsbury Town | 1:0 | ||||
| 10. Round | 29/09/2018 | Burton Albion | - | Scunthorpe United | 0:0 |  |
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| 14. Round | 20/10/2018 | Wycombe Wanderers | - | Scunthorpe United | 3:2 | ||||
| 15. Round | 23/10/2018 | Blackpool FC | - | Scunthorpe United | 1:0 | ||||
| 16. Round | 27/10/2018 | Scunthorpe United | - | Plymouth Argyle | 1:4 | ||||
| 17. Round | 03/11/2018 | Scunthorpe United | - | Oxford United | 3:3 | ||||
| 18. Round | 17/11/2018 | Bristol Rovers | - | Scunthorpe United | 1:2 | ||||
| 19. Round | 24/11/2018 | Scunthorpe United | - | Portsmouth FC | 1:2 | ||||
| 20. Round | 27/11/2018 | Southend United | - | Scunthorpe United | 2:0 | ||||
| 21. Round | 08/12/2018 | Scunthorpe United | - | Gillingham FC | 0:2 | ||||
| 22. Round | 15/12/2018 | Doncaster Rovers | - | Scunthorpe United | 3:0 | ||||
| 23. Round | 22/12/2018 | Bradford City | - | Scunthorpe United | 2:0 |
England