| Middlesbrough FC v Liverpool FC 17/08/1996 | View match | |
| Chelsea FC v Middlesbrough FC 21/08/1996 | £3.50 | |
| Nottingham Forest FC v Middlesbrough FC 24/08/1996 | View match | |
| Middlesbrough FC v West Ham United FC 04/09/1996 | View match | |
| Middlesbrough FC v Coventry City FC 07/09/1996 | View match | |
| Everton FC v Middlesbrough FC 14/09/1996 | £4.50 | |
| Middlesbrough FC v Hereford United 18/09/1996 | View match | |
| Middlesbrough FC v Arsenal FC 21/09/1996 | View match | |
| Hereford United v Middlesbrough FC 24/09/1996 | View match | |
| Southampton FC v Middlesbrough FC 28/09/1996 | £1.50 | |
| Sunderland FC v Middlesbrough FC 14/10/1996 | View match | |
| Middlesbrough FC v Tottenham Hotspur FC 19/10/1996 | £5.00 |