| 1. Ronde | 16.08.2008 | Sunderland AFC | - | Liverpool FC | 0:1 | ||||
| 3. Ronde | 31.08.2008 | Sunderland AFC | - | Manchester City | 0:3 |  |
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| 4. Ronde | 13.09.2008 | Wigan Athletic | - | Sunderland AFC | 1:1 | ||||
| 5. Ronde | 20.09.2008 | Sunderland AFC | - | Middlesbrough FC | 2:0 | ||||
| 6. Ronde | 27.09.2008 | Aston Villa | - | Sunderland AFC | 2:1 | ||||
| 7. Ronde | 04.10.2008 | Sunderland AFC | - | Arsenal FC | 1:1 | ||||
| 8. Ronde | 18.10.2008 | Fulham FC | - | Sunderland AFC | 0:0 | ||||
| 9. Ronde | 25.10.2008 | Sunderland AFC | - | Newcastle United | 2:1 | ||||
| 11. Ronde | 01.11.2008 | Chelsea FC | - | Sunderland AFC | 5:0 | ||||
| 15. Ronde | 29.11.2008 | Sunderland AFC | - | Bolton Wanderers | 1:4 | |
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| 16. Ronde | 06.12.2008 | Manchester United | - | Sunderland AFC | 1:0 | ||||
| 21. Ronde | 10.01.2009 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
| 22. Ronde | 17.01.2009 | Sunderland AFC | - | Aston Villa | 1:2 |
Guadeloupe