| Norwich City FC v Middlesbrough FC 17/04/1965 | View match | |
| Middlesbrough FC v Leyton Orient FC 19/04/1965 | View match | |
| Middlesbrough FC v Charlton Athletic FC 24/04/1965 | View match | |
| Middlesbrough FC v Manchester City FC 21/08/1965 | View match | |
| Birmingham City FC v Middlesbrough FC 23/08/1965 | £2.50 | |
| Huddersfield Town FC v Middlesbrough FC 28/08/1965 | View match | |
| Middlesbrough FC v Birmingham City FC 31/08/1965 | View match | |
| Middlesbrough FC v Crystal Palace FC 04/09/1965 | View match | |
| Ipswich Town FC v Middlesbrough FC 07/09/1965 | View match | |
| Preston North End FC v Middlesbrough FC 11/09/1965 | £5.00 | |
| Preston North End FC v Middlesbrough FC 11/09/1965 | £4.50 | |
| Middlesbrough FC v Ipswich Town FC 14/09/1965 | View match |