1. Round | 15/08/1998 | Sheffield Wednesday | - | West Ham United | 0:1 | ||||
2. Round | 22/08/1998 | Tottenham Hotspur | - | Sheffield Wednesday | 0:3 | ||||
3. Round | 29/08/1998 | Sheffield Wednesday | - | Aston Villa | 0:1 | ||||
4. Round | 09/09/1998 | Derby County | - | Sheffield Wednesday | 1:0 | ||||
5. Round | 12/09/1998 | Sheffield Wednesday | - | Blackburn Rovers | 3:0 | ||||
6. Round | 19/09/1998 | Wimbledon FC | - | Sheffield Wednesday | 2:1 | ||||
7. Round | 26/09/1998 | Sheffield Wednesday | - | Arsenal FC | 1:0 | ||||
8. Round | 03/10/1998 | Middlesbrough FC | - | Sheffield Wednesday | 4:0 | ||||
9. Round | 18/10/1998 | Coventry City | - | Sheffield Wednesday | 1:0 | ||||
10. Round | 24/10/1998 | Sheffield Wednesday | - | Everton FC | 0:0 | ||||
11. Round | 31/10/1998 | Sheffield Wednesday | - | Southampton FC | 0:0 | ||||
12. Round | 08/11/1998 | Leeds United | - | Sheffield Wednesday | 2:1 | ||||
23. Round | 30/01/1999 | Sheffield Wednesday | - | Derby County | 0:1 | ||||
26. Round | 20/02/1999 | Blackburn Rovers | - | Sheffield Wednesday | 1:4 | ||||
27. Round | 27/02/1999 | Sheffield Wednesday | - | Middlesbrough FC | 3:1 |