| 1. Round | 11/08/2007 | Sunderland AFC | - | Tottenham Hotspur | 1:0 | ||||
| 2. Round | 15/08/2007 | Birmingham City | - | Sunderland AFC | 2:2 | ||||
| 13. Round | 10/11/2007 | Sunderland AFC | - | Newcastle United | 1:1 | ||||
| 14. Round | 24/11/2007 | Everton FC | - | Sunderland AFC | 7:1 | ||||
| 15. Round | 01/12/2007 | Sunderland AFC | - | Derby County | 1:0 | ||||
| 30. Round | 15/03/2008 | Sunderland AFC | - | Chelsea FC | 0:1 | ||||
| 31. Round | 22/03/2008 | Aston Villa | - | Sunderland AFC | 0:1 | ||||
| 32. Round | 29/03/2008 | Sunderland AFC | - | West Ham United | 2:1 | ||||
| 33. Round | 05/04/2008 | Fulham FC | - | Sunderland AFC | 1:3 | ||||
| 34. Round | 12/04/2008 | Sunderland AFC | - | Manchester City | 1:2 | ||||
| 35. Round | 20/04/2008 | Newcastle United | - | Sunderland AFC | 2:0 | ||||
| 36. Round | 26/04/2008 | Sunderland AFC | - | Middlesbrough FC | 3:2 | ||||
| 38. Round | 11/05/2008 | Sunderland AFC | - | Arsenal FC | 0:1 |
Trinidad & Tobago