| 1. Jornada | 07.08.1999 | Sheffield Wednesday | - | Liverpool | 1:2 |  |
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| 2. Jornada | 11.08.1999 | Manchester United | - | Sheffield Wednesday | 4:0 | ||||
| 3. Jornada | 14.08.1999 | Bradford City | - | Sheffield Wednesday | 1:1 | ||||
| 4. Jornada | 21.08.1999 | Sheffield Wednesday | - | Tottenham Hotspur | 1:2 | |
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| 5. Jornada | 25.08.1999 | Sheffield Wednesday | - | Derby County | 0:2 | ||||
| 7. Jornada | 11.09.1999 | Sheffield Wednesday | - | Everton | 0:2 | ||||
| 8. Jornada | 19.09.1999 | Newcastle United | - | Sheffield Wednesday | 8:0 |
Italia