| 3. Journée | 22.08.2008 | Southend United | - | Brighton & Hove Albion | 0:2 |  |
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| 4. Journée | 30.08.2008 | Walsall FC | - | Southend United | 5:2 | |
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| 6. Journée | 13.09.2008 | Southend United | - | Hereford United | 1:0 | ||||
| 7. Journée | 20.09.2008 | Crewe Alexandra | - | Southend United | 3:4 | ||||
| 8. Journée | 26.09.2008 | Southend United | - | Leyton Orient | 3:0 |  |
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| 9. Journée | 04.10.2008 | Yeovil Town | - | Southend United | 1:2 | ||||
| 10. Journée | 11.10.2008 | Southend United | - | Stockport County | 1:1 | ||||
| 11. Journée | 18.10.2008 | Southend United | - | Swindon Town | 2:1 | ||||
| 12. Journée | 21.10.2008 | Scunthorpe United | - | Southend United | 1:1 | ||||
| 14. Journée | 28.10.2008 | Southend United | - | Leeds United | 1:0 | ||||
| 15. Journée | 01.11.2008 | Southend United | - | Colchester United | 3:3 | ||||
| 16. Journée | 15.11.2008 | Tranmere Rovers | - | Southend United | 2:2 | |
Angleterre