| Arsenal FC v Leicester City FC 07/08/1999 | £1.50 | |
| Leicester City FC v Coventry City FC 11/08/1999 | View match | |
| Leicester City FC v Chelsea FC 14/08/1999 | £3.50 | |
| West Ham United FC v Leicester City FC 21/08/1999 | View match | |
| Middlesbrough FC v Leicester City FC 24/08/1999 | View match | |
| Leicester City FC v Watford FC 30/08/1999 | View match | |
| Sunderland FC v Leicester City FC 11/09/1999 | View match | |
| Crystal Palace FC v Leicester City FC 14/09/1999 | View match | |
| Leicester City FC v Liverpool FC 18/09/1999 | View match | |
| Leicester City FC v Crystal Palace FC 22/09/1999 | View match | |
| Leicester City FC v Aston Villa FC 25/09/1999 | View match | |
| Tottenham Hotspur FC v Leicester City FC 03/10/1999 | £5.50 |