| 1. Round | 07/08/2009 | Middlesbrough FC | - | Sheffield United | 0:0 | ||||
| 8. Round | 19/09/2009 | Middlesbrough FC | - | West Bromwich Albion | 0:5 | ||||
| 10. Round | 29/09/2009 | Middlesbrough FC | - | Leicester City | 0:1 | ||||
| 12. Round | 17/10/2009 | Middlesbrough FC | - | Watford FC | 0:1 | ||||
| 13. Round | 20/10/2009 | Middlesbrough FC | - | Derby County | 2:0 | ||||
| 14. Round | 24/10/2009 | Preston North End | - | Middlesbrough FC | 2:2 |  |
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| 17. Round | 21/11/2009 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
| 19. Round | 05/12/2009 | Queens Park Rangers | - | Middlesbrough FC | 1:5 | ||||
| 20. Round | 08/12/2009 | Middlesbrough FC | - | Blackpool FC | 0:3 |
France