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 | ||||
23. Round | 28/12/2008 | Milton Keynes Dons | - | Southend United | 2:0 | ||||
26. Round | 17/01/2009 | Stockport County | - | Southend United | 3:1 |