| 1. Round | 15/08/1998 | Manchester United | - | Leicester City | 2:2 | ||||
| 4. Round | 09/09/1998 | Leicester City | - | Middlesbrough FC | 0:1 | ||||
| 6. Round | 19/09/1998 | Derby County | - | Leicester City | 2:0 | ||||
| 7. Round | 27/09/1998 | Leicester City | - | Wimbledon FC | 1:1 | ||||
| 10. Round | 24/10/1998 | Aston Villa | - | Leicester City | 1:1 | ||||
| 11. Round | 31/10/1998 | Leicester City | - | Liverpool FC | 1:0 | ||||
| 12. Round | 07/11/1998 | Charlton Athletic | - | Leicester City | 0:0 | ||||
| 13. Round | 14/11/1998 | West Ham United | - | Leicester City | 3:2 | ||||
| 22. Round | 16/01/1999 | Leicester City | - | Manchester United | 2:6 |
England