| 22. Jornada | 26.12.2008 | Southend United | - | Northampton Town | 1:0 | ||||
| 26. Jornada | 17.01.2009 | Stockport County | - | Southend United | 3:1 |  |
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| 24. Jornada | 20.01.2009 | Leyton Orient | - | Southend United | 1:1 | ||||
| 27. Jornada | 24.01.2009 | Southend United | - | Yeovil Town | 0:1 | ||||
| 28. Jornada | 27.01.2009 | Leeds United | - | Southend United | 2:0 | ||||
| 35. Jornada | 03.03.2009 | Southend United | - | Millwall FC | 0:1 |
Inglaterra