| 1. Round | 09/08/2008 | Cardiff City | - | Southampton FC | 2:1 | ||||
| 2. Round | 16/08/2008 | Southampton FC | - | Birmingham City | 1:2 | ||||
| 3. Round | 23/08/2008 | Derby County | - | Southampton FC | 0:1 | ||||
| 4. Round | 30/08/2008 | Southampton FC | - | Blackpool FC | 0:1 | ||||
| 5. Round | 14/09/2008 | Queens Park Rangers | - | Southampton FC | 4:1 | ||||
| 24. Round | 20/12/2008 | Southampton FC | - | Nottingham Forest | 0:2 | ||||
| 25. Round | 26/12/2008 | Plymouth Argyle | - | Southampton FC | 2:0 | ||||
| 26. Round | 28/12/2008 | Southampton FC | - | Reading FC | 1:1 | ||||
| 27. Round | 10/01/2009 | Barnsley FC | - | Southampton FC | 0:1 | ||||
| 28. Round | 17/01/2009 | Southampton FC | - | Doncaster Rovers | 1:2 | ||||
| 29. Round | 27/01/2009 | Norwich City | - | Southampton FC | 2:2 |
England