| 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 | ||||
| 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 | 12.01.2000 | Bolton Wanderers | - | Tranmere Rovers | 0:1 | ||||
| Demi-finales | 26.01.2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |
Islande