| 1. Round | 07/08/1999 | West Ham United | - | Tottenham Hotspur | 1:0 | ||||
| 14. Round | 07/11/1999 | Tottenham Hotspur | - | Arsenal FC | 2:1 |  |
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| 15. Round | 20/11/1999 | Southampton FC | - | Tottenham Hotspur | 0:1 | ||||
| 16. Round | 28/11/1999 | Newcastle United | - | Tottenham Hotspur | 2:1 | |
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| 18. Round | 18/12/1999 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
| 5. Round | 12/01/2000 | Chelsea FC | - | Tottenham Hotspur | 1:0 | ||||
| 22. Round | 15/01/2000 | Everton FC | - | Tottenham Hotspur | 2:2 | |
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| 23. Round | 22/01/2000 | Tottenham Hotspur | - | Sheffield Wednesday | 0:1 |
England