| 4e tour | 24.01.2009 | Wolverhampton Wanderers | - | Middlesbrough FC | 1:2 | ||||
| tour des 16 | 14.02.2009 | West Ham United | - | Middlesbrough FC | 1:1 | ||||
| tour des 16 | 25.02.2009 | Middlesbrough FC | - | West Ham United | 2:0 |  |
|||
| Quarts de finale | 08.03.2009 | Everton FC | - | Middlesbrough FC | 2:1 |
Turquie