| 27. Round | 05/01/2019 | Scunthorpe United | - | Coventry City | 2:1 | ||||
| 28. Round | 12/01/2019 | Walsall FC | - | Scunthorpe United | 1:2 | ||||
| 29. Round | 19/01/2019 | Scunthorpe United | - | Sunderland AFC | 1:1 | ||||
| 30. Round | 26/01/2019 | Fleetwood Town | - | Scunthorpe United | 0:1 | ||||
| 31. Round | 02/02/2019 | Barnsley FC | - | Scunthorpe United | 2:0 |  |
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| 32. Round | 09/02/2019 | Scunthorpe United | - | Accrington Stanley | 2:0 | ||||
| 33. Round | 16/02/2019 | Gillingham FC | - | Scunthorpe United | 1:0 | ||||
| 34. Round | 23/02/2019 | Scunthorpe United | - | Doncaster Rovers | 1:1 | ||||
| 36. Round | 09/03/2019 | Scunthorpe United | - | Bristol Rovers | 0:1 | |
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| 37. Round | 12/03/2019 | Scunthorpe United | - | Southend United | 4:1 |  |
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| 38. Round | 16/03/2019 | Portsmouth FC | - | Scunthorpe United | 2:0 | ||||
| 39. Round | 23/03/2019 | Rochdale AFC | - | Scunthorpe United | 3:1 | |
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| 40. Round | 30/03/2019 | Scunthorpe United | - | AFC Wimbledon | 1:2 | ||||
| 41. Round | 06/04/2019 | Shrewsbury Town | - | Scunthorpe United | 1:1 |
England