1. Round | 07/08/1999 | Portsmouth FC | - | Sheffield United | 2:0 | ||||
2. Round | 14/08/1999 | Sheffield United | - | Walsall FC | 1:1 | ||||
8. Round | 18/09/1999 | Sheffield United | - | Charlton Athletic | 1:2 | ||||
17. Round | 06/11/1999 | Barnsley FC | - | Sheffield United | 2:0 |