| 1. Round | 07/08/1999 | Birmingham City | - | Fulham FC | 2:2 | ||||
| 2. Round | 14/08/1999 | Norwich City | - | Birmingham City | 0:1 | ||||
| 3. Round | 21/08/1999 | Birmingham City | - | Port Vale FC | 4:2 | ||||
| 4. Round | 27/08/1999 | Stockport County | - | Birmingham City | 2:0 | ||||
| 5. Round | 30/08/1999 | Birmingham City | - | Crewe Alexandra | 5:1 | ||||
| 6. Round | 05/09/1999 | Bolton Wanderers | - | Birmingham City | 3:3 | ||||
| 7. Round | 11/09/1999 | Birmingham City | - | West Bromwich Albion | 1:1 | ||||
| 8. Round | 18/09/1999 | Ipswich Town | - | Birmingham City | 0:1 | ||||
| 9. Round | 25/09/1999 | Birmingham City | - | Queens Park Rangers | 2:0 | ||||
| 10. Round | 02/10/1999 | Charlton Athletic | - | Birmingham City | 1:0 | ||||
| 11. Round | 08/10/1999 | Walsall FC | - | Birmingham City | 1:0 | ||||
| 20. Round | 23/11/1999 | Birmingham City | - | Tranmere Rovers | 3:1 | ||||
| 21. Round | 27/11/1999 | Birmingham City | - | Swindon Town | 1:1 | ||||
| 22. Round | 04/12/1999 | Fulham FC | - | Birmingham City | 0:0 | ||||
| 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 |
England