1. Round | 09/08/1999 | Sheffield United | - | Shrewsbury Town | 3:0 | ||||
1. Round | 23/08/1999 | Shrewsbury Town | - | Sheffield United | 0:3 | ||||
2. Round | 13/09/1999 | Sheffield United | - | Preston North End | 2:0 | ||||
2. Round | 20/09/1999 | Preston North End | - | Sheffield United | 3:0 |