| 1. Jornada | 07.08.1999 | Grimsby Town | - | Stockport County | 0:1 | ||||
| 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 | ||||
| 20. Jornada | 23.11.1999 | West Bromwich Albion | - | Stockport County | 2:0 |
Inglaterra