| 1. Round | 09/08/2008 | Cardiff City | - | Southampton FC | 2:1 | ||||
| 2. Round | 16/08/2008 | Southampton FC | - | Birmingham City | 1:2 | ||||
| 7. Round | 20/09/2008 | Southampton FC | - | Barnsley FC | 0:0 | ||||
| 11. Round | 18/10/2008 | Southampton FC | - | Watford FC | 0:3 | ||||
| 14. Round | 28/10/2008 | Southampton FC | - | Coventry City | 1:1 | ||||
| 15. Round | 01/11/2008 | Preston North End | - | Southampton FC | 2:3 | ||||
| 16. Round | 08/11/2008 | Southampton FC | - | Bristol City | 0:1 | ||||
| 39. Round | 14/03/2009 | Southampton FC | - | Queens Park Rangers | 0:0 | ||||
| 40. Round | 21/03/2009 | Blackpool FC | - | Southampton FC | 1:1 | ||||
| 41. Round | 04/04/2009 | Southampton FC | - | Charlton Athletic | 2:3 |
England