1. Round | 07/08/1999 | Sheffield Wednesday | - | Liverpool FC | 1:2 | ||||
2. Round | 11/08/1999 | Manchester United | - | Sheffield Wednesday | 4:0 | ||||
3. Round | 14/08/1999 | Bradford City | - | Sheffield Wednesday | 1:1 | ![]() |
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5. Round | 25/08/1999 | Sheffield Wednesday | - | Derby County | 0:2 | ||||
6. Round | 28/08/1999 | Southampton FC | - | Sheffield Wednesday | 2:0 | ||||
8. Round | 19/09/1999 | Newcastle United | - | Sheffield Wednesday | 8:0 |