1. Round | 07/08/1999 | Sheffield Wednesday | - | Liverpool FC | 1:2 | ||||
3. Round | 14/08/1999 | Bradford City | - | Sheffield Wednesday | 1:1 | ||||
6. Round | 28/08/1999 | Southampton FC | - | Sheffield Wednesday | 2:0 | ||||
7. Round | 11/09/1999 | Sheffield Wednesday | - | Everton FC | 0:2 | ||||
8. Round | 19/09/1999 | Newcastle United | - | Sheffield Wednesday | 8:0 | ||||
9. Round | 25/09/1999 | Sunderland AFC | - | Sheffield Wednesday | 1:0 | ||||
10. Round | 02/10/1999 | Sheffield Wednesday | - | Wimbledon FC | 5:1 | ||||
22. Round | 15/01/2000 | Sheffield Wednesday | - | Bradford City | 2:0 | ||||
23. Round | 22/01/2000 | Tottenham Hotspur | - | Sheffield Wednesday | 0:1 | ||||
16. Round | 02/02/2000 | Sheffield Wednesday | - | Manchester United | 0:1 | ||||
24. Round | 05/02/2000 | Derby County | - | Sheffield Wednesday | 3:3 | ||||
25. Round | 12/02/2000 | Sheffield Wednesday | - | Southampton FC | 0:1 |