2. Round | 21/09/1998 | Wimbledon FC | - | Portsmouth FC | 4:1 aet | ||||
Round of 16 | 09/11/1998 | Bolton Wanderers | - | Wimbledon FC | 1:2 | ||||
Semi-finals | 26/01/1999 | Tottenham Hotspur | - | Wimbledon FC | 0:0 | ||||
Semi-finals | 15/02/1999 | Wimbledon FC | - | Tottenham Hotspur | 0:1 |