| 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 |  |
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| 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 | ||||
| 18. Round | 19/12/1998 | Chelsea FC | - | Tottenham Hotspur | 2:0 | ||||
| 21. Round | 09/01/1999 | Sheffield Wednesday | - | 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 | ||||
| 27. Round | 27/02/1999 | Tottenham Hotspur | - | Derby County | 1:1 |  |
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| 28. Round | 10/03/1999 | Leeds United | - | Tottenham Hotspur | 2:0 | ||||
| 31. Round | 03/04/1999 | Tottenham Hotspur | - | Leicester City | 0:2 | |
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| 38. Round | 16/05/1999 | Manchester United | - | Tottenham Hotspur | 2:1 |
England