| 1. Round | 09/08/1999 | Halifax Town | - | West Bromwich Albion | 0:0 | ||||
| 1. Round | 23/08/1999 | West Bromwich Albion | - | Halifax Town | 5:1 | ||||
| 2. Round | 13/09/1999 | West Bromwich Albion | - | Wycombe Wanderers | 1:1 | ||||
| 2. Round | 20/09/1999 | Wycombe Wanderers | - | West Bromwich Albion | 3:4 aet |  |
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| 3. Round | 11/10/1999 | West Bromwich Albion | - | Fulham FC | 1:2 |
England