| 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 |  |
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| 15. Round | 22/10/2019 | Scunthorpe United | - | Exeter City | 3:1 | ||||
| 17. Round | 02/11/2019 | Scunthorpe United | - | Stevenage FC | 0:0 | ||||
| 20. Round | 07/12/2019 | Forest Green Rovers | - | Scunthorpe United | 0:2 |  |
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| 22. Round | 21/12/2019 | Grimsby Town | - | Scunthorpe United | 0:1 | ||||
| 23. Round | 26/12/2019 | Scunthorpe United | - | Walsall FC | 0:2 | ||||
| 24. Round | 29/12/2019 | Crewe Alexandra | - | Scunthorpe United | 3:1 | ||||
| 25. Round | 01/01/2020 | Oldham Athletic | - | Scunthorpe United | 0:2 | ||||
| 26. Round | 04/01/2020 | Scunthorpe United | - | Plymouth Argyle | 1:3 | ||||
| 31. Round | 01/02/2020 | Crawley Town | - | Scunthorpe United | 3:1 | |
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| 32. Round | 08/02/2020 | Scunthorpe United | - | Cheltenham Town | 1:0 | ||||
| 33. Round | 11/02/2020 | Scunthorpe United | - | Cambridge United | 0:2 | ||||
| 34. Round | 03/03/2020 | Swindon Town | - | Scunthorpe United | 2:0 | ||||
| 37. Round | 07/03/2020 | Scunthorpe United | - | Grimsby Town | 0:2 |  |
England