3. Round | 22/08/2008 | Southend United | - | Brighton & Hove Albion | 0:2 | ||||
4. Round | 30/08/2008 | Walsall FC | - | Southend United | 5:2 | ||||
5. Round | 06/09/2008 | Carlisle United | - | Southend United | 2:1 | ||||
6. Round | 13/09/2008 | Southend United | - | Hereford United | 1:0 | ||||
7. Round | 20/09/2008 | Crewe Alexandra | - | Southend United | 3:4 | ||||
8. Round | 26/09/2008 | Southend United | - | Leyton Orient | 3:0 | ||||
9. Round | 04/10/2008 | Yeovil Town | - | Southend United | 1:2 | ||||
10. Round | 11/10/2008 | Southend United | - | Stockport County | 1:1 | ||||
11. Round | 18/10/2008 | Southend United | - | Swindon Town | 2:1 | ||||
12. Round | 21/10/2008 | Scunthorpe United | - | Southend United | 1:1 | ||||
13. Round | 25/10/2008 | Bristol Rovers | - | Southend United | 4:2 | ||||
14. Round | 28/10/2008 | Southend United | - | Leeds United | 1:0 | ||||
15. Round | 01/11/2008 | Southend United | - | Colchester United | 3:3 | ||||
16. Round | 15/11/2008 | Tranmere Rovers | - | Southend United | 2:2 |