| 1. Round | 09/08/2009 | Coventry City | - | Ipswich Town | 2:1 | ||||
| 2. Round | 15/08/2009 | Ipswich Town | - | Leicester City | 0:0 | ||||
| 3. Round | 18/08/2009 | Ipswich Town | - | Crystal Palace | 1:3 | ||||
| 4. Round | 22/08/2009 | West Bromwich Albion | - | Ipswich Town | 2:0 | ||||
| 5. Round | 29/08/2009 | Ipswich Town | - | Preston North End | 1:1 | ||||
| 9. Round | 26/09/2009 | Ipswich Town | - | Newcastle United | 0:4 | ||||
| 25. Round | 10/01/2010 | Leicester City | - | Ipswich Town | 1:1 | ||||
| 27. Round | 26/01/2010 | Ipswich Town | - | West Bromwich Albion | 1:1 | ||||
| 28. Round | 30/01/2010 | Preston North End | - | Ipswich Town | 2:0 |
Netherlands