| 1. Round | 03/08/2019 | Scunthorpe United | - | Swindon Town | 0:2 | ||||
| 2. Round | 10/08/2019 | Cheltenham Town | - | Scunthorpe United | 4:1 | ||||
| 4. Round | 20/08/2019 | Cambridge United | - | Scunthorpe United | 3:2 | ||||
| 5. Round | 24/08/2019 | Macclesfield Town | - | Scunthorpe United | 1:0 | ||||
| 6. Round | 31/08/2019 | Scunthorpe United | - | Carlisle United | 0:1 |  |
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| 7. Round | 07/09/2019 | Mansfield Town | - | Scunthorpe United | 2:0 | |
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| 18. Round | 16/11/2019 | Leyton Orient | - | Scunthorpe United | 0:2 | ||||
| 19. Round | 23/11/2019 | Scunthorpe United | - | Port Vale FC | 2:1 | ||||
| 20. Round | 07/12/2019 | Forest Green Rovers | - | Scunthorpe United | 0:2 | ||||
| 21. Round | 14/12/2019 | Scunthorpe United | - | Colchester United | 2:2 | |
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| 27. Round | 11/01/2020 | Scunthorpe United | - | Newport County | 1:2 | ||||
| 28. Round | 18/01/2020 | Bradford City | - | Scunthorpe United | 2:2 |
England