7. Round | 11/09/1999 | Arsenal FC | - | Aston Villa | 3:1 | ||||
8. Round | 18/09/1999 | Aston Villa | - | Bradford City | 1:0 | ||||
9. Round | 25/09/1999 | Leicester City | - | Aston Villa | 3:1 | ||||
10. Round | 02/10/1999 | Aston Villa | - | Liverpool FC | 0:0 | ||||
26. Round | 26/02/2000 | Bradford City | - | Aston Villa | 1:1 | ||||
27. Round | 05/03/2000 | Aston Villa | - | Arsenal FC | 1:1 | ||||
28. Round | 11/03/2000 | Aston Villa | - | Coventry City | 1:0 | ||||
35. Round | 15/03/2000 | Liverpool FC | - | Aston Villa | 0:0 | ||||
29. Round | 18/03/2000 | Southampton FC | - | Aston Villa | 2:0 | ||||
38. Round | 14/05/2000 | Aston Villa | - | Manchester United | 0:1 |