| Aston Villa FC v Leeds United FC 17/02/1999 | £3.00 | |
| Tottenham Hotspur FC v Leeds United FC 24/02/1999 | £6.50 | |
| Leeds United FC v Tottenham Hotspur FC 10/03/1999 | £5.00 | |
| Charlton Athletic FC v Leeds United FC 17/04/1999 | £3.00 | |
| Chelsea FC v Leeds United FC 05/05/1999 | £3.50 | |
| Chelsea FC v Leeds United FC 05/05/1999 | £3.00 | |
| Southampton FC v Leeds United FC 11/08/1999 | £3.50 | |
| Tottenham Hotspur FC v Leeds United FC 28/08/1999 | £4.00 | |
| Tottenham Hotspur FC v Leeds United FC 28/08/1999 | £5.00 | |
| Leeds United FC v FK Partizan Belgrade 30/09/1999 | £3.00 | |
| Chelsea FC v Leeds United FC 19/12/1999 | £3.00 | |
| Arsenal FC v Leeds United FC 28/12/1999 | £3.00 |