1. Round | 16/08/2008 | Sunderland AFC | - | Liverpool FC | 0:1 | ||||
2. Round | 23/08/2008 | Tottenham Hotspur | - | Sunderland AFC | 1:2 | ||||
3. Round | 31/08/2008 | Sunderland AFC | - | Manchester City | 0:3 | ||||
4. Round | 13/09/2008 | Wigan Athletic | - | Sunderland AFC | 1:1 | ||||
5. Round | 20/09/2008 | Sunderland AFC | - | Middlesbrough FC | 2:0 | ||||
11. Round | 01/11/2008 | Chelsea FC | - | Sunderland AFC | 5:0 | ||||
12. Round | 08/11/2008 | Sunderland AFC | - | Portsmouth FC | 1:2 | ||||
13. Round | 15/11/2008 | Blackburn Rovers | - | Sunderland AFC | 1:2 | ||||
14. Round | 23/11/2008 | Sunderland AFC | - | West Ham United | 0:1 | ||||
15. Round | 29/11/2008 | Sunderland AFC | - | Bolton Wanderers | 1:4 | ||||
17. Round | 13/12/2008 | Sunderland AFC | - | West Bromwich Albion | 4:0 | ||||
18. Round | 20/12/2008 | Hull City | - | Sunderland AFC | 1:4 | ||||
19. Round | 26/12/2008 | Sunderland AFC | - | Blackburn Rovers | 0:0 | ||||
20. Round | 28/12/2008 | Everton FC | - | Sunderland AFC | 3:0 | ||||
21. Round | 10/01/2009 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
22. Round | 17/01/2009 | Sunderland AFC | - | Aston Villa | 1:2 |