| 17. Jornada | 22.11.2008 | Southend United | - | Oldham Athletic | 1:2 | ||||
| 18. Jornada | 25.11.2008 | Cheltenham Town | - | Southend United | 0:0 | ||||
| 19. Jornada | 06.12.2008 | Leicester City | - | Southend United | 3:0 | ||||
| 20. Jornada | 13.12.2008 | Southend United | - | Huddersfield Town | 0:1 |  |
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| 21. Jornada | 19.12.2008 | Hartlepool United | - | Southend United | 3:0 | ||||
| 22. Jornada | 26.12.2008 | Southend United | - | Northampton Town | 1:0 | |
Inglaterra