1. Round | 07/08/1999 | Grimsby Town | - | Stockport County | 0:1 | ||||
2. Round | 14/08/1999 | Stockport County | - | Tranmere Rovers | 2:1 | ||||
3. Round | 21/08/1999 | Portsmouth FC | - | Stockport County | 2:0 | ||||
4. Round | 27/08/1999 | Stockport County | - | Birmingham City | 2:0 | ||||
20. Round | 23/11/1999 | West Bromwich Albion | - | Stockport County | 2:0 |