| Bury FC v Middlesbrough FC 30/10/1965 | £10.00 | |
| Middlesbrough FC v Southampton FC 06/11/1965 | View match | |
| Derby County FC v Middlesbrough FC 13/11/1965 | View match | |
| Middlesbrough FC v Cardiff City FC 20/11/1965 | View match | |
| Middlesbrough FC v Coventry City FC 04/12/1965 | View match | |
| Bristol City FC v Middlesbrough FC 11/12/1965 | View match | |
| Darlington FC v Middlesbrough FC 13/12/1965 | View match | |
| Middlesbrough FC v Wolverhampton Wanderers FC 18/12/1965 | View match | |
| Middlesbrough FC v Leyton Orient FC 27/12/1965 | View match | |
| Rotherham United FC v Middlesbrough FC 01/01/1966 | View match | |
| Middlesbrough FC v Derby County FC 08/01/1966 | View match | |
| Tottenham Hotspur FC v Middlesbrough FC 22/01/1966 | £1.50 |