| 3. Round | 07/01/2006 | Nuneaton Borough AFC | - | Middlesbrough FC | 1:1 | ||||
| 4. Round | 28/01/2006 | Coventry City | - | Middlesbrough FC | 1:1 | ||||
| 4. Round | 08/02/2006 | Middlesbrough FC | - | Coventry City | 1:0 | ||||
| Round of 16 | 19/02/2006 | Preston North End | - | Middlesbrough FC | 0:2 | ||||
| Quarter-finals | 23/03/2006 | Charlton Athletic | - | Middlesbrough FC | 0:0 | ||||
| Quarter-finals | 12/04/2006 | Middlesbrough FC | - | Charlton Athletic | 4:2 | ||||
| Semi-finals | 23/04/2006 | Middlesbrough FC | - | West Ham United | 0:1 |
England
