| 5. Round | 11/09/2000 | Tottenham Hotspur | - | West Ham United | 1:0 | ||||
| 6. Round | 16/09/2000 | Charlton Athletic | - | Tottenham Hotspur | 1:0 | ||||
| 7. Round | 23/09/2000 | Tottenham Hotspur | - | Manchester City | 0:0 | ||||
| 8. Round | 30/09/2000 | Leeds United | - | Tottenham Hotspur | 4:3 |  |
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| 9. Round | 14/10/2000 | Coventry City | - | Tottenham Hotspur | 2:1 | |
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| 10. Round | 21/10/2000 | Tottenham Hotspur | - | Derby County | 3:1 | ||||
| 11. Round | 28/10/2000 | Chelsea FC | - | Tottenham Hotspur | 3:0 | ||||
| 12. Round | 04/11/2000 | Tottenham Hotspur | - | Sunderland AFC | 2:1 | ||||
| 13. Round | 11/11/2000 | Aston Villa | - | Tottenham Hotspur | 2:0 | |
Switzerland
Spain