3. Round | 03/01/2009 | Middlesbrough FC | - | Barrow AFC | 2:1 | ||||
4. Round | 24/01/2009 | Wolverhampton Wanderers | - | Middlesbrough FC | 1:2 | ||||
Round of 16 | 14/02/2009 | West Ham United | - | Middlesbrough FC | 1:1 |
3. Round | 03/01/2009 | Middlesbrough FC | - | Barrow AFC | 2:1 | ||||
4. Round | 24/01/2009 | Wolverhampton Wanderers | - | Middlesbrough FC | 1:2 | ||||
Round of 16 | 14/02/2009 | West Ham United | - | Middlesbrough FC | 1:1 |