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 | ||||
33. Round | 27/02/2000 | Birmingham City | - | Ipswich Town | 1:1 | ||||
35. Round | 07/03/2000 | Birmingham City | - | Portsmouth FC | 1:0 | ||||
38. Round | 22/03/2000 | Blackburn Rovers | - | Birmingham City | 1:0 | ||||
45. Round | 28/04/2000 | Manchester City | - | Birmingham City | 1:0 |