1. Round | 09/08/1999 | Preston North End | - | Wrexham AFC | 1:0 | ||||
2. Round | 13/09/1999 | Sheffield United | - | Preston North End | 2:0 | ||||
2. Round | 20/09/1999 | Preston North End | - | Sheffield United | 3:0 | ||||
3. Round | 11/10/1999 | Arsenal FC | - | Preston North End | 2:1 |