| Middlesbrough FC v Leicester City FC 18/11/2000 | View match | |
| Middlesbrough FC v Bradford City FC 25/11/2000 | View match | |
| West Ham United FC v Middlesbrough FC 02/12/2000 | £5.50 | |
| Sunderland FC v Middlesbrough FC 09/12/2000 | View match | |
| Middlesbrough FC v Chelsea FC 16/12/2000 | £4.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 23/12/2000 | £4.00 | |
| Tottenham Hotspur FC v Middlesbrough FC 23/12/2000 | £4.50 | |
| Middlesbrough FC v Liverpool FC 26/12/2000 | View match | |
| Middlesbrough FC v Coventry City FC 30/12/2000 | View match | |
| Leeds United FC v Middlesbrough FC 01/01/2001 | View match | |
| Bradford City FC v Middlesbrough FC 08/01/2001 | View match | |
| Middlesbrough FC v Derby County FC 13/01/2001 | View match |