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 | ||||
6. Round | 28/08/1999 | Southampton FC | - | Sheffield Wednesday | 2:0 | ||||
7. Round | 11/09/1999 | Sheffield Wednesday | - | Everton FC | 0:2 | ||||
9. Round | 25/09/1999 | Sunderland AFC | - | Sheffield Wednesday | 1:0 | ||||
12. Round | 23/10/1999 | Sheffield Wednesday | - | Coventry City | 0:0 | ||||
17. Round | 05/12/1999 | Liverpool FC | - | Sheffield Wednesday | 4:1 | ||||
20. Round | 29/12/1999 | Chelsea FC | - | Sheffield Wednesday | 3:0 | ||||
21. Round | 03/01/2000 | Sheffield Wednesday | - | Arsenal FC | 1:1 | ||||
27. Round | 04/03/2000 | Everton FC | - | Sheffield Wednesday | 1:1 | ||||
31. Round | 05/04/2000 | Sheffield Wednesday | - | Aston Villa | 0:1 | ||||
35. Round | 12/04/2000 | Wimbledon FC | - | Sheffield Wednesday | 0:2 | ||||
33. Round | 15/04/2000 | Sheffield Wednesday | - | Chelsea FC | 1:0 | ||||
36. Round | 30/04/2000 | Sheffield Wednesday | - | Leeds United | 0:3 | ||||
32. Round | 09/05/2000 | Arsenal FC | - | Sheffield Wednesday | 3:3 |