| Middlesbrough FC v Manchester United FC 10/04/2000 | View match | |
| Coventry City FC v Middlesbrough FC 15/04/2000 | View match | |
| Chelsea FC v Middlesbrough FC 22/04/2000 | £3.00 | |
| Chelsea FC v Middlesbrough FC 22/04/2000 | £3.00 | |
| West Ham United FC v Middlesbrough FC 29/04/2000 | £5.00 | |
| 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 | £4.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 22/08/2000 | £5.00 |