8. Round | 18/09/1999 | Aston Villa | - | Bradford City | 1:0 | ||||
9. Round | 25/09/1999 | Leicester City | - | Aston Villa | 3:1 | ||||
15. Round | 22/11/1999 | Coventry City | - | Aston Villa | 2:1 | ||||
16. Round | 27/11/1999 | Everton FC | - | Aston Villa | 0:0 | ||||
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 | ||||
23. Round | 22/01/2000 | Aston Villa | - | Chelsea FC | 0:0 | ||||
29. Round | 18/03/2000 | Southampton FC | - | Aston Villa | 2:0 | ||||
31. Round | 05/04/2000 | Sheffield Wednesday | - | Aston Villa | 0:1 | ||||
32. Round | 09/04/2000 | Aston Villa | - | Leeds United | 1:0 | ||||
33. Round | 15/04/2000 | Tottenham Hotspur | - | Aston Villa | 2:4 | ||||
34. Round | 22/04/2000 | Aston Villa | - | Leicester City | 2:2 |