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