| 6. Ronde | 19.09.1998 | Wimbledon FC | - | Sheffield Wednesday | 2:1 | ||||
| 7. Ronde | 27.09.1998 | Leicester City | - | Wimbledon FC | 1:1 | ||||
| 10. Ronde | 24.10.1998 | Wimbledon FC | - | Middlesbrough FC | 2:2 | ||||
| 11. Ronde | 31.10.1998 | Wimbledon FC | - | Blackburn Rovers | 1:1 | ||||
| 18. Ronde | 19.12.1998 | Southampton FC | - | Wimbledon FC | 3:1 | ||||
| 19. Ronde | 26.12.1998 | Wimbledon FC | - | Charlton Athletic | 2:1 | ||||
| 20. Ronde | 29.12.1998 | Leeds United | - | Wimbledon FC | 2:2 |  |
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| 21. Ronde | 09.01.1999 | Wimbledon FC | - | Derby County | 2:1 | ||||
| 24. Ronde | 08.02.1999 | Charlton Athletic | - | Wimbledon FC | 2:0 | ||||
| 31. Ronde | 03.04.1999 | Wimbledon FC | - | Manchester United | 1:1 |  |
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| 32. Ronde | 05.04.1999 | Middlesbrough FC | - | Wimbledon FC | 3:1 | |
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| 33. Ronde | 11.04.1999 | Wimbledon FC | - | Chelsea FC | 1:2 | ||||
| 34. Ronde | 19.04.1999 | Arsenal FC | - | Wimbledon FC | 5:1 | |
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| 35. Ronde | 24.04.1999 | Wimbledon FC | - | Newcastle United | 1:1 | ||||
| 37. Ronde | 08.05.1999 | Wimbledon FC | - | Southampton FC | 0:2 | ||||
| 38. Ronde | 16.05.1999 | Liverpool FC | - | Wimbledon FC | 3:0 |
Engeland