| 19. Jornada | 06.12.2008 | Leicester City | - | Southend United | 3:0 | ||||
| 20. Jornada | 13.12.2008 | Southend United | - | Huddersfield Town | 0:1 | ||||
| 21. Jornada | 19.12.2008 | Hartlepool United | - | Southend United | 3:0 | ||||
| 22. Jornada | 26.12.2008 | Southend United | - | Northampton Town | 1:0 |  |
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| 23. Jornada | 28.12.2008 | Milton Keynes Dons | - | Southend United | 2:0 | ||||
| 26. Jornada | 17.01.2009 | Stockport County | - | Southend United | 3:1 |
Inglaterra
Santa Lucía