10. Round | 02/10/1999 | Charlton Athletic | - | Birmingham City | 1:0 | ||||
12. Round | 16/10/1999 | Birmingham City | - | Crystal Palace | 2:0 | ||||
14. Round | 23/10/1999 | Grimsby Town | - | Birmingham City | 1:1 | ||||
15. Round | 27/10/1999 | Queens Park Rangers | - | Birmingham City | 2:2 |