| 2e tour | 14.09.1999 | Chester City | - | Aston Villa | 0:1 |  |
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| 2e tour | 21.09.1999 | Aston Villa | - | Chester City | 5:0 |  |
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| 3e tour | 13.10.1999 | Aston Villa | - | Manchester United | 3:0 | |
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| tour des 16 | 01.12.1999 | Aston Villa | - | Southampton FC | 4:0 | ||||
| Quarts de finale | 11.01.2000 | West Ham United | - | Aston Villa | 1:3 ap | |
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| Demi-finales | 25.01.2000 | Aston Villa | - | Leicester City | 0:0 | ||||
| Demi-finales | 02.02.2000 | Leicester City | - | Aston Villa | 1:0 |
Angleterre