| 3e Ronde | 21.12.1999 | Bolton Wanderers | - | Cardiff City | 1:0 | ||||
| 4e Ronde | 08.01.2000 | Grimsby Town | - | Bolton Wanderers | 0:2 | ||||
| Achtste finale | 29.01.2000 | Cambridge United | - | Bolton Wanderers | 1:3 |  |
|||
| Kwartfinale | 19.02.2000 | Bolton Wanderers | - | Charlton Athletic | 1:0 |
Engeland