| 1. Round | 07/08/1998 | Bradford City | - | Stockport County | 1:2 | ||||
| 2. Round | 14/08/1998 | Stockport County | - | Norwich City | 0:2 | ||||
| 9. Round | 18/09/1998 | Queens Park Rangers | - | Stockport County | 2:0 | ||||
| 11. Round | 28/09/1998 | Stockport County | - | Huddersfield Town | 1:1 | ||||
| 12. Round | 02/10/1998 | Swindon Town | - | Stockport County | 2:3 | ||||
| 14. Round | 16/10/1998 | Bury FC | - | Stockport County | 1:1 | ||||
| 15. Round | 19/10/1998 | Sheffield United | - | Stockport County | 1:1 | ||||
| 17. Round | 30/10/1998 | Tranmere Rovers | - | Stockport County | 1:1 | ||||
| 32. Round | 19/02/1999 | Crewe Alexandra | - | Stockport County | 0:2 |
Wales