| Leyton Orient FC v Middlesbrough FC 28/09/1957 | £10.00 | |
| Leyton Orient FC v Middlesbrough FC 28/09/1957 | £10.00 | |
| Middlesbrough FC v Charlton Athletic FC 05/10/1957 | View match | |
| Middlesbrough FC v Fulham FC 12/10/1957 | View match | |
| Swansea Town v Middlesbrough FC 19/10/1957 | View match | |
| Middlesbrough FC v Derby County FC 26/10/1957 | View match | |
| Middlesbrough FC v Newcastle United FC 30/10/1957 | View match | |
| Bristol Rovers FC v Middlesbrough FC 02/11/1957 | View match | |
| Middlesbrough FC v Lincoln City FC 09/11/1957 | View match | |
| Middlesbrough FC v Cologne (Koln) 13/11/1957 | View match | |
| Notts County FC v Middlesbrough FC 16/11/1957 | View match | |
| Middlesbrough FC v Ipswich Town FC 23/11/1957 | View match |