| 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 | ||||
| 6. Round | 27/09/2008 | Aston Villa | - | Sunderland AFC | 2:1 | ||||
| 7. Round | 04/10/2008 | Sunderland AFC | - | Arsenal FC | 1:1 | ||||
| 8. Round | 18/10/2008 | Fulham FC | - | Sunderland AFC | 0:0 | ||||
| 15. Round | 29/11/2008 | Sunderland AFC | - | Bolton Wanderers | 1:4 | ||||
| 31. Round | 04/04/2009 | West Ham United | - | Sunderland AFC | 2:0 | ||||
| 32. Round | 11/04/2009 | Sunderland AFC | - | Manchester United | 1:2 | ||||
| 33. Round | 18/04/2009 | Sunderland AFC | - | Hull City | 1:0 |
Scotland
