| 17. Round | 15/11/2008 | Doncaster Rovers | - | Ipswich Town | 1:0 | ||||
| 18. Round | 22/11/2008 | Ipswich Town | - | Derby County | 2:0 | ||||
| 19. Round | 25/11/2008 | Birmingham City | - | Ipswich Town | 2:1 | ||||
| 20. Round | 29/11/2008 | Ipswich Town | - | Sheffield United | 1:1 | ||||
| 21. Round | 07/12/2008 | Norwich City | - | Ipswich Town | 2:0 | ||||
| 22. Round | 10/12/2008 | Ipswich Town | - | Bristol City | 3:1 | ||||
| 23. Round | 13/12/2008 | Ipswich Town | - | Cardiff City | 1:2 | ||||
| 24. Round | 20/12/2008 | Coventry City | - | Ipswich Town | 2:2 | ||||
| 25. Round | 26/12/2008 | Ipswich Town | - | Birmingham City | 0:1 |
England