| Cardiff City FC v Middlesbrough FC 07/09/1968 | View match | |
| Middlesbrough FC v Birmingham City FC 14/09/1968 | View match | |
| Bury FC v Middlesbrough FC 21/09/1968 | £4.00 | |
| Middlesbrough FC v Charlton Athletic FC 28/09/1968 | View match | |
| Middlesbrough FC v Derby County FC 05/10/1968 | View match | |
| Huddersfield Town FC v Middlesbrough FC 08/10/1968 | View match | |
| Sheffield United FC v Middlesbrough FC 12/10/1968 | View match | |
| Middlesbrough FC v Fulham FC 19/10/1968 | View match | |
| Oxford United FC v Middlesbrough FC 26/10/1968 | View match | |
| Millwall FC v Middlesbrough FC 09/11/1968 | £4.50 | |
| Middlesbrough FC v Bolton Wanderers FC 16/11/1968 | View match | |
| Aston Villa FC v Middlesbrough FC 23/11/1968 | View match |