| 11. Round | 27/09/2005 | Southend United | - | Yeovil Town | 4:1 | ||||
| 13. Round | 09/10/2005 | Southend United | - | Nottingham Forest | 1:0 | ||||
| 14. Round | 15/10/2005 | Doncaster Rovers | - | Southend United | 2:0 | ||||
| 15. Round | 22/10/2005 | Southend United | - | Barnsley FC | 1:1 |  |
|||
| 16. Round | 29/10/2005 | Bristol City | - | Southend United | 0:3 | ||||
| 17. Round | 12/11/2005 | Southend United | - | Swansea City | 1:2 | |
|||
| 18. Round | 19/11/2005 | Nottingham Forest | - | Southend United | 2:0 | ||||
| 19. Round | 26/11/2005 | Port Vale FC | - | Southend United | 2:1 | ||||
| 20. Round | 06/12/2005 | Southend United | - | Chesterfield FC | 0:0 | ||||
| 21. Round | 10/12/2005 | Southend United | - | Bradford City | 1:1 | ||||
| 22. Round | 17/12/2005 | Huddersfield Town | - | Southend United | 0:0 | ||||
| 23. Round | 26/12/2005 | Southend United | - | Milton Keynes Dons | 0:0 | ||||
| 24. Round | 28/12/2005 | Hartlepool United | - | Southend United | 1:2 |
England