| 8. Round | 18/09/2009 | Sheffield United | - | Sheffield Wednesday | 3:2 |  |
|||
| 10. Round | 29/09/2009 | Sheffield United | - | Ipswich Town | 3:3 | ||||
| 11. Round | 03/10/2009 | Sheffield United | - | Doncaster Rovers | 1:1 | ||||
| 12. Round | 17/10/2009 | Scunthorpe United | - | Sheffield United | 3:1 | ||||
| 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 | ||||
| 18. Round | 28/11/2009 | Bristol City | - | Sheffield United | 2:3 |
England