| 1. Round | 07/08/1998 | Bradford City | - | Stockport County | 1:2 | ||||
| 2. Round | 14/08/1998 | Stockport County | - | Norwich City | 0:2 |  |
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| 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 |  |
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| 5. Round | 30/08/1998 | Wolverhampton Wanderers | - | Stockport County | 2:2 | ||||
| 6. Round | 04/09/1998 | Stockport County | - | Grimsby Town | 2:0 | ||||
| 7. Round | 07/09/1998 | Birmingham City | - | Stockport County | 2:0 | |
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| 8. Round | 11/09/1998 | Stockport County | - | Crewe Alexandra | 1:1 | ||||
| 9. Round | 18/09/1998 | Queens Park Rangers | - | Stockport County | 2:0 | ||||
| 10. Round | 25/09/1998 | Stockport County | - | West Bromwich Albion | 2:2 | |
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| 11. Round | 28/09/1998 | Stockport County | - | Huddersfield Town | 1:1 | ||||
| 27. Round | 08/01/1999 | Stockport County | - | Bradford City | 1:2 |
England