| 7. Round | 07/09/2019 | Mansfield Town | - | Scunthorpe United | 2:0 | ||||
| 8. Round | 14/09/2019 | Scunthorpe United | - | Morecambe FC | 3:0 |  |
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| 9. Round | 17/09/2019 | Scunthorpe United | - | Oldham Athletic | 2:2 |  |
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| 12. Round | 05/10/2019 | Plymouth Argyle | - | Scunthorpe United | 2:2 | ||||
| 13. Round | 12/10/2019 | Scunthorpe United | - | Northampton Town | 3:0 | |
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| 14. Round | 19/10/2019 | Newport County | - | Scunthorpe United | 2:1 | |
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| 15. Round | 22/10/2019 | Scunthorpe United | - | Exeter City | 3:1 | ||||
| 16. Round | 26/10/2019 | Salford City | - | Scunthorpe United | 1:1 | ||||
| 17. Round | 02/11/2019 | Scunthorpe United | - | Stevenage FC | 0:0 | ||||
| 20. Round | 07/12/2019 | Forest Green Rovers | - | Scunthorpe United | 0:2 | ||||
| 22. Round | 21/12/2019 | Grimsby Town | - | Scunthorpe United | 0:1 | ||||
| 23. Round | 26/12/2019 | Scunthorpe United | - | Walsall FC | 0:2 | ||||
| 25. Round | 01/01/2020 | Oldham Athletic | - | Scunthorpe United | 0:2 |
England