| 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 |  |
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| 7. Round | 04/10/2008 | Sunderland AFC | - | Arsenal FC | 1:1 | ||||
| 8. Round | 18/10/2008 | Fulham FC | - | Sunderland AFC | 0:0 | ||||
| 9. Round | 25/10/2008 | Sunderland AFC | - | Newcastle United | 2:1 | ||||
| 10. Round | 29/10/2008 | Stoke City | - | Sunderland AFC | 1:0 | ||||
| 11. Round | 01/11/2008 | Chelsea FC | - | Sunderland AFC | 5:0 | ||||
| 23. Round | 27/01/2009 | Sunderland AFC | - | Fulham FC | 1:0 | ||||
| 24. Round | 01/02/2009 | Newcastle United | - | Sunderland AFC | 1:1 | |
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| 25. Round | 07/02/2009 | Sunderland AFC | - | Stoke City | 2:0 | ||||
| 26. Round | 21/02/2009 | Arsenal FC | - | Sunderland AFC | 0:0 | |
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| 28. Round | 03/03/2009 | Liverpool FC | - | Sunderland AFC | 2:0 | ||||
| 27. Round | 07/03/2009 | Sunderland AFC | - | Tottenham Hotspur | 1:1 | |
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| 29. Round | 14/03/2009 | Sunderland AFC | - | Wigan Athletic | 1:2 | ||||
| 30. Round | 22/03/2009 | Manchester City | - | Sunderland AFC | 1:0 |  |
Northern Ireland
