| 1. Round | 04/08/2018 | Coventry City | - | Scunthorpe United | 1:2 |  |
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| 2. Round | 11/08/2018 | Scunthorpe United | - | Walsall FC | 1:1 | |
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| 3. Round | 19/08/2018 | Sunderland AFC | - | Scunthorpe United | 3:0 | ||||
| 4. Round | 22/08/2018 | Scunthorpe United | - | Fleetwood Town | 0:5 | ||||
| 5. Round | 25/08/2018 | Scunthorpe United | - | Barnsley FC | 2:2 | ||||
| 6. Round | 01/09/2018 | Accrington Stanley | - | Scunthorpe United | 1:1 | ||||
| 11. Round | 02/10/2018 | Scunthorpe United | - | Charlton Athletic | 5:3 | ||||
| 12. Round | 06/10/2018 | Luton Town | - | Scunthorpe United | 3:2 | |
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| 13. Round | 13/10/2018 | Scunthorpe United | - | Peterborough United | 0:2 | ||||
| 14. Round | 20/10/2018 | Wycombe Wanderers | - | Scunthorpe United | 3:2 | |
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| 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 |  |
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| 22. Round | 15/12/2018 | Doncaster Rovers | - | Scunthorpe United | 3:0 | ||||
| 23. Round | 22/12/2018 | Bradford City | - | Scunthorpe United | 2:0 | |
England