| 1. Round | 11/08/2007 | Middlesbrough FC | - | Blackburn Rovers | 1:2 | ||||
| 2. Round | 15/08/2007 | Wigan Athletic | - | Middlesbrough FC | 1:0 | ||||
| 3. Round | 18/08/2007 | Fulham FC | - | Middlesbrough FC | 1:2 | ||||
| 8. Round | 30/09/2007 | Everton FC | - | Middlesbrough FC | 2:0 | ||||
| 9. Round | 07/10/2007 | Manchester City | - | Middlesbrough FC | 3:1 | ||||
| 10. Round | 20/10/2007 | Middlesbrough FC | - | Chelsea FC | 0:2 | ||||
| 12. Round | 03/11/2007 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 | ||||
| 13. Round | 11/11/2007 | Bolton Wanderers | - | Middlesbrough FC | 0:0 | ||||
| 37. Round | 03/05/2008 | Middlesbrough FC | - | Portsmouth FC | 2:0 |  |
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| 38. Round | 11/05/2008 | Middlesbrough FC | - | Manchester City | 8:1 |
England