| 1. Round | 09/08/1999 | Darlington FC | - | Bolton Wanderers | 1:1 | ||||
| 2. Round | 20/09/1999 | Bolton Wanderers | - | Gillingham FC | 2:0 |  |
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| 3. Round | 12/10/1999 | Derby County | - | Bolton Wanderers | 1:2 | ||||
| Semi-finals | 11/01/2000 | Bolton Wanderers | - | Tranmere Rovers | 0:1 | ||||
| Semi-finals | 25/01/2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |
England