| 3e tour | 11.12.1999 | Aston Villa | - | Darlington FC | 2:1 |  |
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| 4e tour | 08.01.2000 | Aston Villa | - | Southampton FC | 1:0 |  |
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| tour des 16 | 31.01.2000 | Aston Villa | - | Leeds United | 3:2 | |
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| Quarts de finale | 20.02.2000 | Everton FC | - | Aston Villa | 1:2 | |
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| Demi-finales | 02.04.2000 | Bolton Wanderers | - | Aston Villa | 1:4 tab | ||||
| Finale | 20.05.2000 | Aston Villa | - | Chelsea FC | 0:1 |
Italie