| Chelsea FC v Middlesbrough FC 22/04/2000 | £3.00 | |
| West Ham United FC v Middlesbrough FC 29/04/2000 | View match | |
| Middlesbrough FC v Newcastle United FC 02/05/2000 | View match | |
| Middlesbrough FC v Watford FC 06/05/2000 | View match | |
| Everton FC v Middlesbrough FC 14/05/2000 | View match | |
| York City FC v Middlesbrough FC 01/08/2000 | View match | |
| Coventry City FC v Middlesbrough FC 19/08/2000 | View match | |
| Middlesbrough FC v Tottenham Hotspur FC 22/08/2000 | £5.00 | |
| Middlesbrough FC v Leeds United FC 26/08/2000 | View match | |
| Derby County FC v Middlesbrough FC 06/09/2000 | View match | |
| Middlesbrough FC v Everton FC 09/09/2000 | View match | |
| Manchester City FC v Middlesbrough FC 17/09/2000 | £2.00 |