| 1er tour | 24.08.1999 | Bolton Wanderers | - | Darlington FC | 5:3 |  |
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| 2e tour | 14.09.1999 | Gillingham FC | - | Bolton Wanderers | 1:4 | ||||
| tour des 16 | 30.11.1999 | Bolton Wanderers | - | Sheffield Wednesday | 1:0 | ||||
| Quarts de finale | 14.12.1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 | ||||
| Demi-finales | 26.01.2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |
Angleterre