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 | ||||
6. Round | 28/09/2008 | Portsmouth FC | - | Tottenham Hotspur | 2:0 | ||||
8. Round | 18/10/2008 | Aston Villa | - | Portsmouth FC | 0:0 | ||||
10. Round | 29/10/2008 | Liverpool FC | - | Portsmouth FC | 1:0 | ||||
11. Round | 01/11/2008 | Portsmouth FC | - | Wigan Athletic | 1:2 | ||||
12. Round | 08/11/2008 | Sunderland AFC | - | Portsmouth FC | 1:2 | ||||
14. Round | 22/11/2008 | Portsmouth FC | - | Hull City | 2:2 | ||||
22. Round | 18/01/2009 | Tottenham Hotspur | - | Portsmouth FC | 1:1 | ||||
23. Round | 27/01/2009 | Portsmouth FC | - | Aston Villa | 0:1 | ||||
24. Round | 31/01/2009 | Fulham FC | - | Portsmouth FC | 3:1 | ||||
28. Round | 03/03/2009 | Portsmouth FC | - | Chelsea FC | 0:1 | ||||
35. Round | 02/05/2009 | Portsmouth FC | - | Arsenal FC | 0:3 | ||||
36. Round | 09/05/2009 | Blackburn Rovers | - | Portsmouth FC | 2:0 | ||||
37. Round | 18/05/2009 | Portsmouth FC | - | Sunderland AFC | 3:1 | ||||
38. Round | 24/05/2009 | Wigan Athletic | - | Portsmouth FC | 1:0 |