| Tercera ronda | 11.12.1999 | Aston Villa | - | Darlington FC | 2:1 | ||||
| Octavos de final | 31.01.2000 | Aston Villa | - | Leeds United | 3:2 | ||||
| Cuartos de final | 20.02.2000 | Everton | - | Aston Villa | 1:2 | ||||
| Semifinales | 02.04.2000 | Bolton Wanderers | - | Aston Villa | 1:4 pn. |  |
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| Final | 20.05.2000 | Aston Villa | - | Chelsea | 0:1 |
Gales