| 26. Round | 12/01/2008 | Southend United | - | Yeovil Town | 1:1 | ||||
| 27. Round | 19/01/2008 | AFC Bournemouth | - | Southend United | 1:4 | ||||
| 25. Round | 22/01/2008 | Hartlepool United | - | Southend United | 4:3 | ||||
| 29. Round | 29/01/2008 | Southend United | - | Leeds United | 1:0 | ||||
| 31. Round | 09/02/2008 | Southend United | - | Hartlepool United | 2:1 | ||||
| 32. Round | 12/02/2008 | Millwall FC | - | Southend United | 2:1 |  |
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| 36. Round | 08/03/2008 | Southend United | - | Luton Town | 2:0 | ||||
| 41. Round | 29/03/2008 | Southend United | - | Walsall FC | 1:0 | ||||
| 45. Round | 26/04/2008 | Tranmere Rovers | - | Southend United | 1:0 |
England