| 1. Round | 07/08/1999 | Leeds United | - | Derby County | 0:0 |  |
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| 2. Round | 11/08/1999 | Southampton FC | - | Leeds United | 0:3 | |
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| 3. Round | 14/08/1999 | Manchester United | - | Leeds United | 2:0 | ||||
| 4. Round | 21/08/1999 | Leeds United | - | Sunderland AFC | 2:1 | |
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| 5. Round | 23/08/1999 | Leeds United | - | Liverpool FC | 1:2 | ||||
| 6. Round | 28/08/1999 | Tottenham Hotspur | - | Leeds United | 1:2 | ||||
| 7. Round | 11/09/1999 | Coventry City | - | Leeds United | 3:4 | ||||
| 8. Round | 19/09/1999 | Leeds United | - | Middlesbrough FC | 2:0 | ||||
| 9. Round | 25/09/1999 | Leeds United | - | Newcastle United | 3:2 | |
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| 10. Round | 03/10/1999 | Watford FC | - | Leeds United | 1:2 | ||||
| 11. Round | 16/10/1999 | Leeds United | - | Sheffield Wednesday | 2:0 | ||||
| 12. Round | 24/10/1999 | Everton FC | - | Leeds United | 4:4 | ||||
| 13. Round | 30/10/1999 | Leeds United | - | West Ham United | 1:0 | ||||
| 14. Round | 07/11/1999 | Wimbledon FC | - | Leeds United | 2:0 | ||||
| 15. Round | 20/11/1999 | Leeds United | - | Bradford City | 2:1 | ||||
| 16. Round | 28/11/1999 | Leeds United | - | Southampton FC | 1:0 |
England