Segunda ronda | 14.09.1999 | Gillingham FC | - | Bolton Wanderers | 1:4 | ||||
Segunda ronda | 21.09.1999 | Bolton Wanderers | - | Gillingham FC | 2:0 | ||||
Tercera ronda | 13.10.1999 | Derby County | - | Bolton Wanderers | 1:2 | ||||
Semifinales | 26.01.2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |