| 1. Round | 07/08/1998 | Wolverhampton Wanderers | - | Tranmere Rovers | 2:0 | ||||
| 2. Round | 14/08/1998 | Oxford United | - | Wolverhampton Wanderers | 0:2 |  |
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| 3. Round | 21/08/1998 | Wolverhampton Wanderers | - | Swindon Town | 1:0 | |
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| 4. Round | 27/08/1998 | Watford FC | - | Wolverhampton Wanderers | 0:2 | ||||
| 5. Round | 30/08/1998 | Wolverhampton Wanderers | - | Stockport County | 2:2 | ||||
| 7. Round | 07/09/1998 | Port Vale FC | - | Wolverhampton Wanderers | 2:1 | ||||
| 8. Round | 11/09/1998 | Wolverhampton Wanderers | - | Sunderland AFC | 1:1 | ||||
| 9. Round | 18/09/1998 | Huddersfield Town | - | Wolverhampton Wanderers | 2:1 |
England