| Middlesbrough FC v Chelsea FC 14/04/1999 | £3.50 | |
| Aston Villa FC v Middlesbrough FC 28/08/1999 | £2.50 | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £4.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 18/12/1999 | £4.50 | |
| Sheffield Wednesday FC v Middlesbrough FC 26/12/1999 | £4.00 | |
| Liverpool FC v Middlesbrough FC 22/01/2000 | £3.50 | |
| Southampton FC v Middlesbrough FC 04/03/2000 | £3.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 03/04/2000 | £4.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 03/04/2000 | £3.00 | |
| Chelsea FC v Middlesbrough FC 22/04/2000 | £3.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 22/08/2000 | £5.00 | |
| Manchester City FC v Middlesbrough FC 17/09/2000 | £2.00 |