17. Round | 22/11/2008 | Southend United | - | Oldham Athletic | 1:2 | ||||
18. Round | 25/11/2008 | Cheltenham Town | - | Southend United | 0:0 | ||||
19. Round | 06/12/2008 | Leicester City | - | Southend United | 3:0 | ||||
20. Round | 13/12/2008 | Southend United | - | Huddersfield Town | 0:1 | ||||
21. Round | 19/12/2008 | Hartlepool United | - | Southend United | 3:0 | ||||
22. Round | 26/12/2008 | Southend United | - | Northampton Town | 1:0 |