1. Round | 15/08/1998 | Middlesbrough FC | - | Leeds United | 0:0 | ![]() |
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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 | ![]() |
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6. Round | 19/09/1998 | Leeds United | - | Aston Villa | 0:0 | ||||
7. Round | 26/09/1998 | Tottenham Hotspur | - | Leeds United | 3:3 | ![]() |
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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 | ![]() |
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11. Round | 31/10/1998 | Derby County | - | Leeds United | 2:2 | ![]() |
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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 | ![]() |
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17. Round | 14/12/1998 | Leeds United | - | Coventry City | 2:0 | ||||
18. Round | 20/12/1998 | Arsenal FC | - | Leeds United | 3:1 |