| 1. Round | 07/08/2009 | Middlesbrough FC | - | Sheffield United | 0:0 | ||||
| 2. Round | 15/08/2009 | Sheffield United | - | Watford FC | 2:0 |  |
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| 3. Round | 18/08/2009 | Sheffield United | - | Leicester City | 1:1 |  |
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| 4. Round | 22/08/2009 | Reading FC | - | Sheffield United | 1:3 | ||||
| 5. Round | 29/08/2009 | Sheffield United | - | West Bromwich Albion | 2:2 | ||||
| 6. Round | 12/09/2009 | Derby County | - | Sheffield United | 0:1 | ||||
| 7. Round | 15/09/2009 | Coventry City | - | Sheffield United | 3:2 | ||||
| 8. Round | 18/09/2009 | Sheffield United | - | Sheffield Wednesday | 3:2 | ||||
| 9. Round | 26/09/2009 | Swansea City | - | Sheffield United | 2:1 | ||||
| 11. Round | 03/10/2009 | Sheffield United | - | Doncaster Rovers | 1:1 | ||||
| 12. Round | 17/10/2009 | Scunthorpe United | - | Sheffield United | 3:1 | ||||
| 13. Round | 20/10/2009 | Blackpool FC | - | Sheffield United | 3:0 | ||||
| 14. Round | 24/10/2009 | Sheffield United | - | Cardiff City | 3:4 | ||||
| 15. Round | 02/11/2009 | Sheffield United | - | Newcastle United | 0:1 | ||||
| 16. Round | 09/11/2009 | Barnsley FC | - | Sheffield United | 2:2 | ||||
| 17. Round | 21/11/2009 | Sheffield United | - | Peterborough United | 1:0 |
Ireland