1. Round | 15/08/1998 | Wimbledon FC | - | Tottenham Hotspur | 3:1 | ||||
4. Round | 09/09/1998 | Tottenham Hotspur | - | Blackburn Rovers | 2:1 | ||||
5. Round | 13/09/1998 | Tottenham Hotspur | - | Middlesbrough FC | 0:3 | ||||
6. Round | 19/09/1998 | Southampton FC | - | Tottenham Hotspur | 1:1 |