| Aston Villa FC v Middlesbrough FC 30/11/1996 | £3.00 | |
| Arsenal FC v Middlesbrough FC 01/01/1997 | £3.00 | |
| Manchester City FC v Middlesbrough FC 15/02/1997 | £6.00 | |
| 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 | |
| Manchester United FC v Middlesbrough FC 05/05/1997 | £5.50 | |
| Manchester United FC v Middlesbrough FC 05/05/1997 | £4.00 | |
| Chelsea FC v Middlesbrough FC 17/05/1997 | £11.50 | |
| Manchester City FC v Middlesbrough FC 20/12/1997 | £4.50 | |
| Aston Villa FC v Middlesbrough FC 23/08/1998 | £4.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 13/09/1998 | £2.00 |