| 16. Round | 17/11/2007 | Southend United | - | Cheltenham Town | 2:2 | ||||
| 18. Round | 05/12/2007 | Southend United | - | Huddersfield Town | 4:1 | ||||
| 19. Round | 08/12/2007 | Southend United | - | Swindon Town | 2:1 | ||||
| 20. Round | 15/12/2007 | Swansea City | - | Southend United | 3:0 | ||||
| 21. Round | 22/12/2007 | Southend United | - | Oldham Athletic | 0:1 | ||||
| 22. Round | 26/12/2007 | Gillingham FC | - | Southend United | 1:1 | ||||
| 23. Round | 29/12/2007 | Doncaster Rovers | - | Southend United | 3:1 | ||||
| 24. Round | 01/01/2008 | Southend United | - | Bristol Rovers | 0:1 |
England