| 2. Round | 14/08/1998 | Stockport County | - | Norwich City | 0:2 | ||||
| 3. Round | 20/08/1998 | Barnsley FC | - | Stockport County | 1:1 |  |
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| 4. Round | 28/08/1998 | Stockport County | - | Crystal Palace | 1:1 | ||||
| 5. Round | 30/08/1998 | Wolverhampton Wanderers | - | Stockport County | 2:2 | ||||
| 10. Round | 25/09/1998 | Stockport County | - | West Bromwich Albion | 2:2 | ||||
| 11. Round | 28/09/1998 | Stockport County | - | Huddersfield Town | 1:1 | ||||
| 12. Round | 02/10/1998 | Swindon Town | - | Stockport County | 2:3 | |
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| 14. Round | 16/10/1998 | Bury FC | - | Stockport County | 1:1 | |
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| 15. Round | 19/10/1998 | Sheffield United | - | Stockport County | 1:1 | ||||
| 16. Round | 23/10/1998 | Stockport County | - | Ipswich Town | 0:1 | ||||
| 17. Round | 30/10/1998 | Tranmere Rovers | - | Stockport County | 1:1 | ||||
| 18. Round | 07/11/1998 | Stockport County | - | Port Vale FC | 4:2 | ||||
| 19. Round | 13/11/1998 | Stockport County | - | Watford FC | 1:1 | ||||
| 20. Round | 20/11/1998 | Bristol City | - | Stockport County | 1:1 |
England