| Huddersfield Town FC v Middlesbrough FC 16/04/1968 | View match | |
| Preston North End FC v Middlesbrough FC 20/04/1968 | View match | |
| Middlesbrough FC v Derby County FC 27/04/1968 | View match | |
| Crystal Palace FC v Middlesbrough FC 04/05/1968 | View match | |
| Middlesbrough FC v Bristol City FC 11/05/1968 | View match | |
| Middlesbrough FC v Heart Of Midlothian (Hearts) 02/08/1968 | View match | |
| Middlesbrough FC v Preston North End FC 10/08/1968 | View match | |
| Norwich City FC v Middlesbrough FC 14/08/1968 | View match | |
| Portsmouth FC v Middlesbrough FC 17/08/1968 | £4.50 | |
| Portsmouth FC v Middlesbrough FC 17/08/1968 | £5.00 | |
| Portsmouth FC v Middlesbrough FC 17/08/1968 | £2.00 | |
| Middlesbrough FC v Crystal Palace FC 20/08/1968 | View match |