| 2. Round | 15/09/1998 | Leicester City | - | Chesterfield FC | 3:0 | ||||
| 2. Round | 21/09/1998 | Chesterfield FC | - | Leicester City | 1:3 |  |
|||
| Round of 16 | 10/11/1998 | Leicester City | - | Leeds United | 2:1 | ||||
| Quarter-finals | 01/12/1998 | Leicester City | - | Blackburn Rovers | 1:0 | ||||
| Semi-finals | 25/01/1999 | Sunderland AFC | - | Leicester City | 1:2 |
England