| 1. Round | 15/08/1998 | Wimbledon FC | - | Tottenham Hotspur | 3:1 | ||||
| 2. Round | 22/08/1998 | Tottenham Hotspur | - | Sheffield Wednesday | 0:3 | ||||
| 3. Round | 29/08/1998 | Everton FC | - | Tottenham Hotspur | 0:1 |  |
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| 4. Round | 09/09/1998 | Tottenham Hotspur | - | Blackburn Rovers | 2:1 | ||||
| 6. Round | 19/09/1998 | Southampton FC | - | Tottenham Hotspur | 1:1 | ||||
| 7. Round | 26/09/1998 | Tottenham Hotspur | - | Leeds United | 3:3 |  |
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| 8. Round | 03/10/1998 | Derby County | - | Tottenham Hotspur | 0:1 | ||||
| 9. Round | 19/10/1998 | Leicester City | - | Tottenham Hotspur | 2:1 | ||||
| 12. Round | 07/11/1998 | Aston Villa | - | Tottenham Hotspur | 3:2 | |
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| 13. Round | 14/11/1998 | Arsenal FC | - | Tottenham Hotspur | 0:0 | ||||
| 22. Round | 16/01/1999 | Tottenham Hotspur | - | Wimbledon FC | 0:0 | ||||
| 23. Round | 30/01/1999 | Blackburn Rovers | - | Tottenham Hotspur | 1:1 | ||||
| 26. Round | 20/02/1999 | Middlesbrough FC | - | Tottenham Hotspur | 0:0 | |
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| 27. Round | 27/02/1999 | Tottenham Hotspur | - | Derby County | 1:1 | ||||
| 25. Round | 02/03/1999 | Tottenham Hotspur | - | Southampton FC | 3:0 | ||||
| 29. Round | 13/03/1999 | Tottenham Hotspur | - | Aston Villa | 1:0 |
Switzerland
Spain