| Chelsea FC v Middlesbrough FC 04/02/1996 | £4.00 | |
| Chelsea FC v Middlesbrough FC 04/02/1996 | £4.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 08/04/1996 | £4.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 08/04/1996 | £2.00 | |
| Chelsea FC v Middlesbrough FC 21/08/1996 | £3.50 | |
| Everton FC v Middlesbrough FC 14/09/1996 | £4.50 | |
| Southampton FC v Middlesbrough FC 28/09/1996 | £1.50 | |
| Middlesbrough FC v Tottenham Hotspur FC 19/10/1996 | £5.00 | |
| Aston Villa FC v Middlesbrough FC 30/11/1996 | £3.00 | |
| Sheffield Wednesday FC v Middlesbrough FC 01/03/1997 | £3.00 | |
| Leicester City FC v Middlesbrough FC 06/04/1997 | £9.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 24/04/1997 | £6.00 |