| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1937/38 | Fifth Round Proper - 1 | 12/02/1938 | York City | 1 - 0 | Middlesbrough | [33] | ||||
| 2 | FA Cup 1966/67 | Second Round Proper - 1 | 07/01/1967 | Middlesbrough | 1 - 1 | York City | [33] | ||||
| 3 | FA Cup 1966/67 | Second Round Proper - 2 | 11/01/1967 | York City | 0 - 0 | Middlesbrough | [33] | ||||
| 4 | FA Cup 1966/67 | Second Round Proper - 2 | 16/01/1967 | Middlesbrough | 4 - 1 | York City | [33] | ||||
| 5 | FA Cup 1969/70 | Fourth Round Proper - 1 | 24/01/1970 | Middlesbrough | 4 - 1 | York City | [33] |
