| 8. Round | 03/10/1998 | Leeds United | - | Leicester City | 0:1 | ||||
| 9. Round | 17/10/1998 | Nottingham Forest | - | Leeds United | 1:1 | ||||
| 10. Round | 25/10/1998 | Leeds United | - | Chelsea FC | 0:0 | ||||
| 11. Round | 31/10/1998 | Derby County | - | Leeds United | 2:2 | ||||
| 12. Round | 08/11/1998 | Leeds United | - | Sheffield Wednesday | 2:1 | ||||
| 15. Round | 29/11/1998 | Manchester United | - | Leeds United | 3:2 | ||||
| 16. Round | 05/12/1998 | Leeds United | - | West Ham United | 4:0 | ||||
| 17. Round | 14/12/1998 | Leeds United | - | Coventry City | 2:0 | ||||
| 19. Round | 26/12/1998 | Newcastle United | - | Leeds United | 0:3 | ||||
| 20. Round | 29/12/1998 | Leeds United | - | Wimbledon FC | 2:2 | ||||
| 21. Round | 09/01/1999 | Blackburn Rovers | - | Leeds United | 1:0 | ||||
| 22. Round | 16/01/1999 | Leeds United | - | Middlesbrough FC | 2:0 | ||||
| 30. Round | 20/03/1999 | Leeds United | - | Derby County | 4:1 | ||||
| 35. Round | 25/04/1999 | Leeds United | - | Manchester United | 1:1 | ||||
| 36. Round | 01/05/1999 | West Ham United | - | Leeds United | 1:5 | ||||
| 32. Round | 05/05/1999 | Chelsea FC | - | Leeds United | 1:0 | ||||
| 38. Round | 16/05/1999 | Coventry City | - | Leeds United | 2:2 |
England