1. Round | 07/08/1999 | Birmingham City | - | Fulham FC | 2:2 | ||||
3. Round | 21/08/1999 | Birmingham City | - | Port Vale FC | 4:2 | ||||
6. Round | 05/09/1999 | Bolton Wanderers | - | Birmingham City | 3:3 | ||||
11. Round | 08/10/1999 | Walsall FC | - | Birmingham City | 1:0 | ||||
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 | ||||
21. Round | 27/11/1999 | Birmingham City | - | Swindon Town | 1:1 | ||||
23. Round | 17/12/1999 | Wolverhampton Wanderers | - | Birmingham City | 2:1 | ||||
24. Round | 26/12/1999 | Birmingham City | - | Sheffield United | 0:2 | ||||
25. Round | 28/12/1999 | Nottingham Forest | - | Birmingham City | 1:0 | ||||
26. Round | 03/01/2000 | Birmingham City | - | Huddersfield Town | 1:0 | ||||
29. Round | 29/01/2000 | Birmingham City | - | Stockport County | 2:1 |