| Wimbledon v Middlesbrough FC 31/10/2000 | View match | |
| Middlesbrough FC v Arsenal FC 04/11/2000 | View match | |
| Manchester United FC v Middlesbrough FC 11/11/2000 | View match | |
| 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 | £2.50 | |
| 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 |