| 2. Round | 19/08/2000 | Stockport County | - | Wolverhampton Wanderers | 1:1 | ||||
| 4. Round | 28/08/2000 | Portsmouth FC | - | Wolverhampton Wanderers | 3:1 | ||||
| 5. Round | 02/09/2000 | Gillingham FC | - | Wolverhampton Wanderers | 1:0 |  |
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| 6. Round | 09/09/2000 | Wolverhampton Wanderers | - | Tranmere Rovers | 1:2 |
England