| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1894/95 | Second Round Proper - 1 | 16/02/1895 | The Wednesday | 6 - 1 | Middlesbrough | [33] | ||||
| 2 | FA Cup 1911/12 | First Round Proper - 1 | 13/01/1912 | Middlesbrough | 0 - 0 | The Wednesday | [33] | ||||
| 3 | FA Cup 1911/12 | First Round Proper - 2 | 25/01/1912 | The Wednesday | 1 - 2 | Middlesbrough | [33] | ||||
| 4 | FA Cup 1959/60 | Third Round Proper - 1 | 09/01/1960 | Sheffield Wednesday | 2 - 1 | Middlesbrough | [33] | ||||
| 5 | FA Cup 1991/92 | Fourth Round Proper - 1 | 04/02/1992 | Sheffield Wednesday | 1 - 2 | Middlesbrough | [33] | ||||
| 6 | FA Cup 2016/17 | Third Round Proper - 1 | 08/01/2017 | Middlesbrough | 3 - 0 | Sheffield Wednesday | [33] |
