Primera ronda | 24.08.1999 | Bolton Wanderers | - | Darlington FC | 5:3 | ||||
Segunda ronda | 21.09.1999 | Bolton Wanderers | - | Gillingham FC | 2:0 | ||||
Tercera ronda | 13.10.1999 | Derby County | - | Bolton Wanderers | 1:2 | ||||
Octavos de final | 30.11.1999 | Bolton Wanderers | - | Sheffield Wednesday | 1:0 | ||||
Cuartos de final | 14.12.1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 |