1. Round | 09/08/1999 | Birmingham City | - | Exeter City | 3:0 | ||||
1. Round | 23/08/1999 | Exeter City | - | Birmingham City | 1:2 | ||||
2. Round | 20/09/1999 | Bristol Rovers | - | Birmingham City | 0:1 | ||||
3. Round | 11/10/1999 | Birmingham City | - | Newcastle United | 2:0 | ||||
Round of 16 | 29/11/1999 | Birmingham City | - | West Ham United | 2:3 |