16. Round | 14/11/2009 | Yeovil Town | - | Southend United | 1:0 | ||||
18. Round | 24/11/2009 | Tranmere Rovers | - | Southend United | 2:0 | ||||
19. Round | 01/12/2009 | Southend United | - | Norwich City | 0:3 | ||||
20. Round | 05/12/2009 | Charlton Athletic | - | Southend United | 1:0 | ||||
21. Round | 12/12/2009 | Southend United | - | Hartlepool United | 3:2 | ||||
22. Round | 19/12/2009 | Exeter City | - | Southend United | 1:0 | ||||
23. Round | 26/12/2009 | Southend United | - | Colchester United | 1:2 | ||||
24. Round | 28/12/2009 | Leyton Orient | - | Southend United | 1:2 |