Primera ronda | 10.08.1999 | Darlington FC | - | Bolton Wanderers | 1:1 | ||||
Primera ronda | 24.08.1999 | Bolton Wanderers | - | Darlington FC | 5:3 | ||||
Segunda ronda | 14.09.1999 | Gillingham FC | - | Bolton Wanderers | 1:4 | ||||
Octavos de final | 30.11.1999 | Bolton Wanderers | - | Sheffield Wednesday | 1:0 | ||||
Cuartos de final | 14.12.1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 | ||||
Semifinales | 12.01.2000 | Bolton Wanderers | - | Tranmere Rovers | 0:1 | ||||
Semifinales | 26.01.2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |