| 1. Round | 15/08/1998 | Sheffield Wednesday | - | West Ham United | 0:1 | ||||
| 2. Round | 22/08/1998 | Tottenham Hotspur | - | Sheffield Wednesday | 0:3 |  |
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| 3. Round | 29/08/1998 | Sheffield Wednesday | - | Aston Villa | 0:1 | ||||
| 4. Round | 09/09/1998 | Derby County | - | Sheffield Wednesday | 1:0 | |
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| 5. Round | 12/09/1998 | Sheffield Wednesday | - | Blackburn Rovers | 3:0 | ||||
| 7. Round | 26/09/1998 | Sheffield Wednesday | - | Arsenal FC | 1:0 | ||||
| 8. Round | 03/10/1998 | Middlesbrough FC | - | Sheffield Wednesday | 4:0 | ||||
| 26. Round | 20/02/1999 | Blackburn Rovers | - | Sheffield Wednesday | 1:4 | ||||
| 36. Round | 01/05/1999 | Nottingham Forest | - | Sheffield Wednesday | 2:0 |
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