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 | ||||
17. Round | 22/11/2008 | Southend United | - | Oldham Athletic | 1:2 |