1. Round | 07/08/1999 | Portsmouth FC | - | Sheffield United | 2:0 | ||||
2. Round | 14/08/1999 | Sheffield United | - | Walsall FC | 1:1 | ||||
3. Round | 21/08/1999 | Manchester City | - | Sheffield United | 6:0 | ||||
5. Round | 30/08/1999 | Tranmere Rovers | - | Sheffield United | 1:3 | ||||
24. Round | 26/12/1999 | Birmingham City | - | Sheffield United | 0:2 | ||||
45. Round | 29/04/2000 | Norwich City | - | Sheffield United | 2:1 |