| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1892/93 | Second Round Proper - 1 | 04/02/1893 | Wolverhampton Wanderers | 2 - 1 | Middlesbrough | [33] | ||||
| 2 | FA Cup 1936/37 | Third Round Proper - 1 | 16/01/1937 | Wolverhampton Wanderers | 6 - 1 | Middlesbrough | [33] | ||||
| 3 | FA Cup 1980/81 | Sixth Round Proper - 1 | 07/03/1981 | Middlesbrough | 1 - 1 | Wolverhampton Wanderers | [33] | ||||
| 4 | FA Cup 1980/81 | Sixth Round Proper - 2 | 10/03/1981 | Wolverhampton Wanderers | 3 - 1 | Middlesbrough | [33] | ||||
| 5 | FA Cup 2008/09 | Fourth Round Proper - 1 | 24/01/2009 | Wolverhampton Wanderers | 1 - 2 | Middlesbrough | [33] |
