1. Round | 17/08/2008 | Chelsea FC | - | Portsmouth FC | 4:0 | ||||
2. Round | 25/08/2008 | Portsmouth FC | - | Manchester United | 0:1 | ||||
3. Round | 30/08/2008 | Everton FC | - | Portsmouth FC | 0:3 | ||||
4. Round | 13/09/2008 | Portsmouth FC | - | Middlesbrough FC | 2:1 | ||||
5. Round | 21/09/2008 | Manchester City | - | Portsmouth FC | 6:0 | ||||
7. Round | 05/10/2008 | Portsmouth FC | - | Stoke City | 2:1 | ||||
8. Round | 18/10/2008 | Aston Villa | - | Portsmouth FC | 0:0 | ||||
9. Round | 26/10/2008 | Portsmouth FC | - | Fulham FC | 1:1 | ||||
10. Round | 29/10/2008 | Liverpool FC | - | Portsmouth FC | 1:0 | ||||
11. Round | 01/11/2008 | Portsmouth FC | - | Wigan Athletic | 1:2 | ||||
13. Round | 15/11/2008 | West Ham United | - | Portsmouth FC | 0:0 | ||||
14. Round | 22/11/2008 | Portsmouth FC | - | Hull City | 2:2 | ||||
15. Round | 30/11/2008 | Portsmouth FC | - | Blackburn Rovers | 3:2 | ||||
16. Round | 07/12/2008 | West Bromwich Albion | - | Portsmouth FC | 1:1 | ||||
18. Round | 20/12/2008 | Bolton Wanderers | - | Portsmouth FC | 2:1 | ||||
20. Round | 28/12/2008 | Arsenal FC | - | Portsmouth FC | 1:0 |