| 1. Jornada | 07.08.1999 | Watford FC | - | Wimbledon FC | 2:3 |  |
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| 2. Jornada | 10.08.1999 | Wimbledon FC | - | Middlesbrough | 2:3 |  |
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| 3. Jornada | 14.08.1999 | Wimbledon FC | - | Coventry City | 1:1 | |
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| 7. Jornada | 11.09.1999 | Wimbledon FC | - | Derby County | 2:2 | |
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| 8. Jornada | 18.09.1999 | Manchester United | - | Wimbledon FC | 1:1 | ||||
| 9. Jornada | 26.09.1999 | Wimbledon FC | - | Tottenham Hotspur | 1:1 | |
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| 10. Jornada | 02.10.1999 | Sheffield Wednesday | - | Wimbledon FC | 5:1 | |
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| 11. Jornada | 16.10.1999 | Wimbledon FC | - | Bradford City | 3:2 | |
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| 12. Jornada | 23.10.1999 | Aston Villa | - | Wimbledon FC | 1:1 | ||||
| 13. Jornada | 30.10.1999 | Wimbledon FC | - | Southampton | 1:1 | ||||
| 14. Jornada | 07.11.1999 | Wimbledon FC | - | Leeds United | 2:0 | |
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| 15. Jornada | 20.11.1999 | Leicester City | - | Wimbledon FC | 2:1 | ||||
| 17. Jornada | 04.12.1999 | Wimbledon FC | - | Watford FC | 5:0 | |
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| 18. Jornada | 18.12.1999 | Arsenal | - | Wimbledon FC | 1:1 | |
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| 36. Jornada | 30.04.2000 | Bradford City | - | Wimbledon FC | 3:0 |  |
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| 37. Jornada | 06.05.2000 | Wimbledon FC | - | Aston Villa | 2:2 | |
Gales