| Middlesbrough FC v Hull City FC 27/01/1968 | £5.00 | |
| Hull City FC v Middlesbrough FC 31/01/1968 | £4.50 | |
| Middlesbrough FC v Hull City FC 03/02/1968 | £4.50 | |
| Hull City FC v Middlesbrough FC 07/02/1968 | £13.50 | |
| Portsmouth FC v Middlesbrough FC 17/08/1968 | £5.00 | |
| Portsmouth FC v Middlesbrough FC 17/08/1968 | £2.00 | |
| Portsmouth FC v Middlesbrough FC 17/08/1968 | £4.50 | |
| Hull City FC v Middlesbrough FC 31/08/1968 | £2.00 | |
| Bury FC v Middlesbrough FC 21/09/1968 | £4.00 | |
| Millwall FC v Middlesbrough FC 09/11/1968 | £4.50 | |
| Fulham FC v Middlesbrough FC 21/12/1968 | £2.50 | |
| Fulham FC v Middlesbrough FC 21/12/1968 | £3.00 |