1. Round | 09/08/1999 | Stockport County | - | Oldham Athletic | 2:0 | ||||
1. Round | 23/08/1999 | Oldham Athletic | - | Stockport County | 1:1 | ||||
2. Round | 13/09/1999 | Barnsley FC | - | Stockport County | 1:1 | ||||
2. Round | 20/09/1999 | Stockport County | - | Barnsley FC | 3:3 aet |