1. Round | 15/08/1998 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
2. Round | 24/08/1998 | Leeds United | - | Blackburn Rovers | 1:0 | ||||
3. Round | 29/08/1998 | Wimbledon FC | - | Leeds United | 1:1 | ||||
4. Round | 08/09/1998 | Leeds United | - | Southampton FC | 3:0 | ||||
5. Round | 12/09/1998 | Everton FC | - | Leeds United | 0:0 | ||||
7. Round | 26/09/1998 | Tottenham Hotspur | - | Leeds United | 3:3 | ||||
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 | ||||
13. Round | 14/11/1998 | Liverpool FC | - | Leeds United | 1:3 | ||||
14. Round | 21/11/1998 | Leeds United | - | Charlton Athletic | 4:1 | ||||
16. Round | 05/12/1998 | Leeds United | - | West Ham United | 4:0 | ||||
24. Round | 06/02/1999 | Leeds United | - | Newcastle United | 0:1 | ||||
35. Round | 25/04/1999 | Leeds United | - | Manchester United | 1:1 | ||||
36. Round | 01/05/1999 | West Ham United | - | Leeds United | 1:5 | ||||
38. Round | 16/05/1999 | Coventry City | - | Leeds United | 2:2 |