| 3. Round | 29/08/1998 | Everton FC | - | Tottenham Hotspur | 0:1 | ||||
| 4. Round | 09/09/1998 | Tottenham Hotspur | - | Blackburn Rovers | 2:1 |  |
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| 5. Round | 13/09/1998 | Tottenham Hotspur | - | Middlesbrough FC | 0:3 | ||||
| 6. Round | 19/09/1998 | Southampton FC | - | Tottenham Hotspur | 1:1 | |
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| 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 |  |
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| 11. Round | 02/11/1998 | Tottenham Hotspur | - | Charlton Athletic | 2:2 | |
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| 13. Round | 14/11/1998 | Arsenal FC | - | Tottenham Hotspur | 0:0 | ||||
| 14. Round | 21/11/1998 | Tottenham Hotspur | - | Nottingham Forest | 2:0 | ||||
| 22. Round | 16/01/1999 | Tottenham Hotspur | - | Wimbledon FC | 0:0 |
Scotland