| 1. Jornada | 07.08.1999 | Grimsby Town | - | Stockport County | 0:1 |  |
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| 2. Jornada | 14.08.1999 | Stockport County | - | Tranmere Rovers | 2:1 | ||||
| 3. Jornada | 21.08.1999 | Portsmouth FC | - | Stockport County | 2:0 | ||||
| 4. Jornada | 27.08.1999 | Stockport County | - | Birmingham City | 2:0 | ||||
| 7. Jornada | 10.09.1999 | Barnsley FC | - | Stockport County | 2:1 | ||||
| 10. Jornada | 02.10.1999 | Walsall FC | - | Stockport County | 1:2 | ||||
| 19. Jornada | 20.11.1999 | Stockport County | - | Sheffield United | 1:1 | ||||
| 29. Jornada | 29.01.2000 | Birmingham City | - | Stockport County | 2:1 |
Inglaterra