| 1. Round | 17/08/2008 | Chelsea FC | - | Portsmouth FC | 4:0 | ||||
| 3. Round | 30/08/2008 | Everton FC | - | Portsmouth FC | 0:3 | ||||
| 8. Round | 18/10/2008 | Aston Villa | - | Portsmouth FC | 0:0 | ||||
| 9. Round | 26/10/2008 | Portsmouth FC | - | Fulham FC | 1:1 | ||||
| 17. Round | 14/12/2008 | Portsmouth FC | - | Newcastle United | 0:3 | ||||
| 20. Round | 28/12/2008 | Arsenal FC | - | Portsmouth FC | 1:0 |
France