4. Round | 28/08/1999 | Sheffield United | - | Ipswich Town | 2:2 | ||||
5. Round | 30/08/1999 | Tranmere Rovers | - | Sheffield United | 1:3 | ||||
6. Round | 04/09/1999 | Sheffield United | - | Crystal Palace | 3:1 | ||||
8. Round | 18/09/1999 | Sheffield United | - | Charlton Athletic | 1:2 | ||||
9. Round | 25/09/1999 | Sheffield United | - | Wolverhampton Wanderers | 3:0 | ||||
10. Round | 02/10/1999 | Huddersfield Town | - | Sheffield United | 4:1 | ||||
11. Round | 09/10/1999 | Crewe Alexandra | - | Sheffield United | 1:0 | ||||
12. Round | 16/10/1999 | Sheffield United | - | Nottingham Forest | 2:1 | ||||
13. Round | 19/10/1999 | Sheffield United | - | Norwich City | 0:0 | ||||
14. Round | 23/10/1999 | Swindon Town | - | Sheffield United | 2:2 |