| 1. Runde | 10.08.1999 | Birmingham City | - | Exeter City | 3:0 |  |
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| 2. Runde | 14.09.1999 | Birmingham City | - | Bristol Rovers | 2:0 | ||||
| 2. Runde | 21.09.1999 | Bristol Rovers | - | Birmingham City | 0:1 | ||||
| 3. Runde | 12.10.1999 | Birmingham City | - | Newcastle United | 2:0 | ||||
| Achtelfinale | 30.11.1999 | Birmingham City | - | West Ham United | 2:3 |
England