4. Round | 22/01/1999 | Wimbledon FC | - | Tottenham Hotspur | 1:1 | ||||
4. Round | 01/02/1999 | Tottenham Hotspur | - | Wimbledon FC | 3:0 | ||||
Round of 16 | 23/02/1999 | Tottenham Hotspur | - | Leeds United | 2:0 | ||||
Quarter-finals | 15/03/1999 | Barnsley FC | - | Tottenham Hotspur | 0:1 |