| Leicester City FC v Middlesbrough FC 05/02/2000 | View match | |
| Middlesbrough FC v Aston Villa FC 14/02/2000 | View match | |
| Middlesbrough FC v Coventry City FC 19/02/2000 | View match | |
| Middlesbrough FC v Leeds United FC 26/02/2000 | View match | |
| Southampton FC v Middlesbrough FC 04/03/2000 | £3.50 | |
| Middlesbrough FC v Arsenal FC 12/03/2000 | View match | |
| Sunderland FC v Middlesbrough FC 18/03/2000 | View match | |
| Middlesbrough FC v Sheffield Wednesday FC 25/03/2000 | View match | |
| Tottenham Hotspur FC v Middlesbrough FC 03/04/2000 | £4.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 03/04/2000 | £3.00 | |
| Middlesbrough FC v Manchester United FC 10/04/2000 | View match | |
| Coventry City FC v Middlesbrough FC 15/04/2000 | View match |