| 1. Round | 03/08/2019 | Scunthorpe United | - | Swindon Town | 0:2 | ||||
| 2. Round | 10/08/2019 | Cheltenham Town | - | Scunthorpe United | 4:1 |  |
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| 6. Round | 31/08/2019 | Scunthorpe United | - | Carlisle United | 0:1 | ||||
| 7. Round | 07/09/2019 | Mansfield Town | - | Scunthorpe United | 2:0 | ||||
| 8. Round | 14/09/2019 | Scunthorpe United | - | Morecambe FC | 3:0 | ||||
| 9. Round | 17/09/2019 | Scunthorpe United | - | Oldham Athletic | 2:2 | |
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| 10. Round | 21/09/2019 | Walsall FC | - | Scunthorpe United | 1:0 | ||||
| 11. Round | 28/09/2019 | Scunthorpe United | - | Bradford City | 1:1 | |
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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 | ||||
| 14. Round | 19/10/2019 | Newport County | - | Scunthorpe United | 2:1 | ||||
| 15. Round | 22/10/2019 | Scunthorpe United | - | Exeter City | 3:1 | |
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| 16. Round | 26/10/2019 | Salford City | - | Scunthorpe United | 1:1 | ||||
| 17. Round | 02/11/2019 | Scunthorpe United | - | Stevenage FC | 0:0 | ||||
| 21. Round | 14/12/2019 | Scunthorpe United | - | Colchester United | 2:2 | ||||
| 22. Round | 21/12/2019 | Grimsby Town | - | Scunthorpe United | 0:1 |
France