1. Round | 07/08/1999 | Leeds United | - | Derby County | 0:0 | ||||
2. Round | 11/08/1999 | Southampton FC | - | Leeds United | 0:3 | ||||
3. Round | 14/08/1999 | Manchester United | - | Leeds United | 2:0 | ||||
4. Round | 21/08/1999 | Leeds United | - | Sunderland AFC | 2:1 | ||||
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 | ||||
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 |