| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 2008/09 | Third Round Proper - 1 | 03/01/2009 | Middlesbrough | 2 - 1 | Barrow | [33] | ||||
| 2 | FA Cup 2008/09 | Fourth Round Proper - 1 | 24/01/2009 | Wolverhampton Wanderers | 1 - 2 | Middlesbrough | [33] | ||||
| 3 | FA Cup 2008/09 | Fifth Round Proper - 1 | 14/02/2009 | West Ham United | 1 - 1 | Middlesbrough | [33] | ||||
| 4 | FA Cup 2008/09 | Fifth Round Proper - 2 | 25/02/2009 | Middlesbrough | 2 - 0 | West Ham United | [33] | ||||
| 5 | FA Cup 2008/09 | Sixth Round Proper - 1 | 08/03/2009 | Everton | 2 - 1 | Middlesbrough | [33] |
