| 2. Round | 13/09/1999 | Chester City | - | Aston Villa | 0:1 |  |
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| 2. Round | 20/09/1999 | Aston Villa | - | Chester City | 5:0 | |
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| 3. Round | 12/10/1999 | Aston Villa | - | Manchester United | 3:0 |  |
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| Round of 16 | 30/11/1999 | Aston Villa | - | Southampton FC | 4:0 | ||||
| Semi-finals | 01/02/2000 | Leicester City | - | Aston Villa | 1:0 |
England