| Chesterfield FC v Middlesbrough FC 14/09/1999 | View match | |
| Leeds United FC v Middlesbrough FC 19/09/1999 | View match | |
| Middlesbrough FC v Chesterfield FC 21/09/1999 | View match | |
| Middlesbrough FC v Chelsea FC 25/09/1999 | View match | |
| Newcastle United FC v Middlesbrough FC 03/10/1999 | View match | |
| Middlesbrough FC v Watford FC 13/10/1999 | View match | |
| Middlesbrough FC v West Ham United FC 17/10/1999 | View match | |
| Watford FC v Middlesbrough FC 24/10/1999 | View match | |
| Middlesbrough FC v Everton FC 30/10/1999 | View match | |
| Middlesbrough FC v Sunderland FC 06/11/1999 | View match | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £2.50 | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £4.00 |