| 5. Jornada | 06.09.2008 | Carlisle United | - | Southend United | 2:1 |  |
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| 6. Jornada | 13.09.2008 | Southend United | - | Hereford United | 1:0 | ||||
| 7. Jornada | 20.09.2008 | Crewe Alexandra | - | Southend United | 3:4 | |
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| 8. Jornada | 26.09.2008 | Southend United | - | Leyton Orient | 3:0 | |
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| 20. Jornada | 13.12.2008 | Southend United | - | Huddersfield Town | 0:1 | ||||
| 22. Jornada | 26.12.2008 | Southend United | - | Northampton Town | 1:0 | ||||
| 23. Jornada | 28.12.2008 | Milton Keynes Dons | - | Southend United | 2:0 |  |
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| 26. Jornada | 17.01.2009 | Stockport County | - | Southend United | 3:1 | ||||
| 24. Jornada | 20.01.2009 | Leyton Orient | - | Southend United | 1:1 | ||||
| 29. Jornada | 31.01.2009 | Southend United | - | Bristol Rovers | 1:0 | |
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| 32. Jornada | 14.02.2009 | Southend United | - | Tranmere Rovers | 2:1 | ||||
| 25. Jornada | 17.02.2009 | Southend United | - | Crewe Alexandra | 0:1 | ||||
| 40. Jornada | 27.03.2009 | Southend United | - | Hartlepool United | 3:2 | ||||
| 42. Jornada | 10.04.2009 | Southend United | - | Milton Keynes Dons | 0:2 | ||||
| 44. Jornada | 18.04.2009 | Southend United | - | Leicester City | 0:2 | ||||
| 45. Jornada | 25.04.2009 | Oldham Athletic | - | Southend United | 1:1 |
Escocia