| Tercera ronda | 21.12.1999 | Bolton Wanderers | - | Cardiff City | 1:0 | ||||
| Cuarta Ronda | 08.01.2000 | Grimsby Town | - | Bolton Wanderers | 0:2 | ||||
| Octavos de final | 29.01.2000 | Cambridge United | - | Bolton Wanderers | 1:3 |  |
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| Cuartos de final | 19.02.2000 | Bolton Wanderers | - | Charlton Athletic | 1:0 | ||||
| Semifinales | 02.04.2000 | Bolton Wanderers | - | Aston Villa | 1:4 pn. | |
Inglaterra