2. Round | 14/09/1998 | Portsmouth FC | - | Wimbledon FC | 2:1 | ||||
2. Round | 21/09/1998 | Wimbledon FC | - | Portsmouth FC | 4:1 aet | ||||
3. Round | 27/10/1998 | Birmingham City | - | Wimbledon FC | 1:2 | ||||
Round of 16 | 09/11/1998 | Bolton Wanderers | - | Wimbledon FC | 1:2 | ||||
Semi-finals | 15/02/1999 | Wimbledon FC | - | Tottenham Hotspur | 0:1 |