8. Round | 19/09/2009 | Brighton & Hove Albion | - | Southend United | 2:3 | ||||
9. Round | 26/09/2009 | Southend United | - | Oldham Athletic | 0:1 | ||||
10. Round | 29/09/2009 | Brentford FC | - | Southend United | 2:1 | ||||
11. Round | 03/10/2009 | Stockport County | - | Southend United | 0:2 | ||||
12. Round | 09/10/2009 | Southend United | - | Southampton FC | 1:3 | ||||
13. Round | 17/10/2009 | Southend United | - | Bristol Rovers | 2:1 |