| 1. Jornada | 07.08.1999 | Sheffield Wednesday | - | Liverpool | 1:2 |  |
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| 3. Jornada | 14.08.1999 | Bradford City | - | Sheffield Wednesday | 1:1 | ||||
| 6. Jornada | 28.08.1999 | Southampton | - | Sheffield Wednesday | 2:0 | ||||
| 7. Jornada | 11.09.1999 | Sheffield Wednesday | - | Everton | 0:2 | |
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| 8. Jornada | 19.09.1999 | Newcastle United | - | Sheffield Wednesday | 8:0 | ||||
| 9. Jornada | 25.09.1999 | Sunderland | - | Sheffield Wednesday | 1:0 | ||||
| 10. Jornada | 02.10.1999 | Sheffield Wednesday | - | Wimbledon FC | 5:1 | ||||
| 22. Jornada | 15.01.2000 | Sheffield Wednesday | - | Bradford City | 2:0 | ||||
| 23. Jornada | 22.01.2000 | Tottenham Hotspur | - | Sheffield Wednesday | 0:1 | ||||
| 16. Jornada | 02.02.2000 | Sheffield Wednesday | - | Manchester United | 0:1 | ||||
| 24. Jornada | 05.02.2000 | Derby County | - | Sheffield Wednesday | 3:3 |  |
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| 25. Jornada | 12.02.2000 | Sheffield Wednesday | - | Southampton | 0:1 |
Escocia