| 2. Runde | 16.09.1998 | Leicester City | - | Chesterfield FC | 3:0 | ||||
| 2. Runde | 22.09.1998 | Chesterfield FC | - | Leicester City | 1:3 | ||||
| 3. Runde | 27.10.1998 | Charlton Athletic | - | Leicester City | 1:2 | ||||
| Achtelfinale | 11.11.1998 | Leicester City | - | Leeds United | 2:1 | ||||
| Viertelfinale | 02.12.1998 | Leicester City | - | Blackburn Rovers | 1:0 | ||||
| Halbfinale | 17.02.1999 | Leicester City | - | Sunderland AFC | 1:1 | ||||
| Finale | 21.03.1999 | Leicester City | - | Tottenham Hotspur | 0:1 |  |
Wales