6. Round | 28/08/1999 | Aston Villa | - | Middlesbrough FC | 1:0 | ||||
7. Round | 11/09/1999 | Arsenal FC | - | Aston Villa | 3:1 | ||||
8. Round | 18/09/1999 | Aston Villa | - | Bradford City | 1:0 | ||||
11. Round | 18/10/1999 | Sunderland AFC | - | Aston Villa | 2:1 | ||||
15. Round | 22/11/1999 | Coventry City | - | Aston Villa | 2:1 | ||||
18. Round | 18/12/1999 | Aston Villa | - | Sheffield Wednesday | 2:1 | ||||
19. Round | 26/12/1999 | Derby County | - | Aston Villa | 0:2 | ||||
20. Round | 29/12/1999 | Aston Villa | - | Tottenham Hotspur | 1:1 | ||||
21. Round | 03/01/2000 | Leeds United | - | Aston Villa | 1:2 | ||||
22. Round | 15/01/2000 | West Ham United | - | Aston Villa | 1:1 | ||||
23. Round | 22/01/2000 | Aston Villa | - | Chelsea FC | 0:0 |