| Leeds United FC v Newcastle United FC 25/09/1999 | View match | |
| Leeds United FC v FK Partizan Belgrade 30/09/1999 | £3.00 | |
| Watford FC v Leeds United FC 03/10/1999 | View match | |
| Leeds United FC v Blackburn Rovers FC 13/10/1999 | View match | |
| Leeds United FC v Sheffield Wednesday FC 16/10/1999 | View match | |
| Leeds United FC v Lokomotiv Moscow 21/10/1999 | View match | |
| Everton FC v Leeds United FC 24/10/1999 | View match | |
| Leeds United FC v West Ham United FC 30/10/1999 | View match | |
| Lokomotiv Moscow v Leeds United FC 04/11/1999 | View match | |
| Wimbledon v Leeds United FC 07/11/1999 | View match | |
| Leeds United FC v Bradford City FC 20/11/1999 | View match | |
| Leeds United FC v Southampton FC 28/11/1999 | £3.00 |