2e tour | 14.09.1999 | Gillingham FC | - | Bolton Wanderers | 1:4 | ||||
2e tour | 21.09.1999 | Bolton Wanderers | - | Gillingham FC | 2:0 | ||||
3e tour | 13.10.1999 | Derby County | - | Bolton Wanderers | 1:2 | ||||
Demi-finales | 26.01.2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |