| 11. Round | 13/10/2007 | Southend United | - | Crewe Alexandra | 3:0 | ||||
| 14. Round | 03/11/2007 | Northampton Town | - | Southend United | 0:1 | ||||
| 15. Round | 06/11/2007 | Nottingham Forest | - | Southend United | 4:1 | ||||
| 16. Round | 17/11/2007 | Southend United | - | Cheltenham Town | 2:2 | ||||
| 20. Round | 15/12/2007 | Swansea City | - | Southend United | 3:0 |  |
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| 21. Round | 22/12/2007 | Southend United | - | Oldham Athletic | 0:1 | ||||
| 29. Round | 29/01/2008 | Southend United | - | Leeds United | 1:0 | ||||
| 32. Round | 12/02/2008 | Millwall FC | - | Southend United | 2:1 | ||||
| 34. Round | 23/02/2008 | Yeovil Town | - | Southend United | 0:3 | ||||
| 36. Round | 08/03/2008 | Southend United | - | Luton Town | 2:0 | ||||
| 37. Round | 11/03/2008 | Southend United | - | Nottingham Forest | 1:1 | ||||
| 38. Round | 15/03/2008 | Huddersfield Town | - | Southend United | 1:2 | ||||
| 41. Round | 29/03/2008 | Southend United | - | Walsall FC | 1:0 | ||||
| 42. Round | 05/04/2008 | Crewe Alexandra | - | Southend United | 1:3 | ||||
| 45. Round | 26/04/2008 | Tranmere Rovers | - | Southend United | 1:0 | ||||
| 46. Round | 03/05/2008 | Southend United | - | Port Vale FC | 1:1 |
Belgium