| Preston North End FC v Middlesbrough FC 11/09/1965 | £5.00 | |
| Middlesbrough FC v Ipswich Town FC 14/09/1965 | View match | |
| Middlesbrough FC v Charlton Athletic FC 18/09/1965 | View match | |
| Colchester United FC v Middlesbrough FC 22/09/1965 | View match | |
| Plymouth Argyle FC v Middlesbrough FC 25/09/1965 | View match | |
| Middlesbrough FC v Rotherham United FC 09/10/1965 | View match | |
| Middlesbrough FC v Millwall FC 13/10/1965 | View match | |
| Wolverhampton Wanderers FC v Middlesbrough FC 16/10/1965 | View match | |
| Millwall FC v Middlesbrough FC 18/10/1965 | View match | |
| Middlesbrough FC v Norwich City FC 22/10/1965 | View match | |
| Middlesbrough FC v Portsmouth FC 26/10/1965 | View match | |
| Bury FC v Middlesbrough FC 30/10/1965 | £10.00 |