3. Round | 29/08/1998 | Everton FC | - | Tottenham Hotspur | 0:1 | ||||
4. Round | 09/09/1998 | Tottenham Hotspur | - | Blackburn Rovers | 2:1 | ||||
5. Round | 13/09/1998 | Tottenham Hotspur | - | Middlesbrough FC | 0:3 | ||||
7. Round | 26/09/1998 | Tottenham Hotspur | - | Leeds United | 3:3 | ||||
8. Round | 03/10/1998 | Derby County | - | Tottenham Hotspur | 0:1 | ||||
9. Round | 19/10/1998 | Leicester City | - | Tottenham Hotspur | 2:1 | ||||
10. Round | 24/10/1998 | Tottenham Hotspur | - | Newcastle United | 2:0 | ||||
11. Round | 02/11/1998 | Tottenham Hotspur | - | Charlton Athletic | 2:2 | ||||
12. Round | 07/11/1998 | Aston Villa | - | Tottenham Hotspur | 3:2 | ||||
13. Round | 14/11/1998 | Arsenal FC | - | Tottenham Hotspur | 0:0 | ||||
14. Round | 21/11/1998 | Tottenham Hotspur | - | Nottingham Forest | 2:0 | ||||
15. Round | 28/11/1998 | West Ham United | - | Tottenham Hotspur | 2:1 |