| 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 | £3.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 03/04/2000 | £4.50 | |
| 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 | |
| Southampton FC v Middlesbrough FC 30/09/2000 | £2.50 | |
| Southampton FC v Middlesbrough FC 30/09/2000 | £2.50 | |
| Charlton Athletic FC v Middlesbrough FC 21/10/2000 | £5.50 | |
| Ipswich Town FC v Middlesbrough FC 28/10/2000 | £4.50 | |
| West Ham United FC v Middlesbrough FC 02/12/2000 | £5.50 |