14. Round | 23/10/1999 | Grimsby Town | - | Birmingham City | 1:1 | ||||
15. Round | 27/10/1999 | Queens Park Rangers | - | Birmingham City | 2:2 | ||||
16. Round | 30/10/1999 | Birmingham City | - | Charlton Athletic | 1:0 | ||||
17. Round | 06/11/1999 | Portsmouth FC | - | Birmingham City | 2:2 | ||||
19. Round | 20/11/1999 | Barnsley FC | - | Birmingham City | 2:1 | ||||
20. Round | 23/11/1999 | Birmingham City | - | Tranmere Rovers | 3:1 | ||||
21. Round | 27/11/1999 | Birmingham City | - | Swindon Town | 1:1 |