| 23. Round | 22/01/2000 | Tottenham Hotspur | - | Sheffield Wednesday | 0:1 | ||||
| 24. Round | 05/02/2000 | Tottenham Hotspur | - | Chelsea FC | 0:1 | ||||
| 25. Round | 12/02/2000 | Leeds United | - | Tottenham Hotspur | 1:0 | ||||
| 29. Round | 19/03/2000 | Arsenal FC | - | Tottenham Hotspur | 2:1 | ||||
| 31. Round | 03/04/2000 | Tottenham Hotspur | - | Middlesbrough FC | 2:3 | ||||
| 35. Round | 19/04/2000 | Leicester City | - | Tottenham Hotspur | 0:1 | ||||
| 34. Round | 22/04/2000 | Tottenham Hotspur | - | Wimbledon FC | 2:0 | ||||
| 36. Round | 29/04/2000 | Tottenham Hotspur | - | Derby County | 1:1 |  |
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| 37. Round | 06/05/2000 | Manchester United | - | Tottenham Hotspur | 3:1 |
Netherlands