1. Round | 07/08/1999 | Newcastle United | - | Aston Villa | 0:1 | ||||
2. Round | 11/08/1999 | Aston Villa | - | Everton FC | 3:0 | ||||
3. Round | 16/08/1999 | Aston Villa | - | West Ham United | 2:2 | ||||
4. Round | 21/08/1999 | Chelsea FC | - | Aston Villa | 1:0 | ||||
5. Round | 24/08/1999 | Watford FC | - | Aston Villa | 0:1 | ||||
6. Round | 28/08/1999 | Aston Villa | - | Middlesbrough FC | 1:0 | ||||
7. Round | 11/09/1999 | Arsenal FC | - | Aston Villa | 3:1 | ||||
9. Round | 25/09/1999 | Leicester City | - | Aston Villa | 3:1 | ||||
11. Round | 18/10/1999 | Sunderland AFC | - | Aston Villa | 2:1 | ||||
12. Round | 23/10/1999 | Aston Villa | - | Wimbledon FC | 1:1 | ||||
13. Round | 30/10/1999 | Manchester United | - | Aston Villa | 3:0 | ||||
14. Round | 06/11/1999 | Aston Villa | - | Southampton FC | 0:1 | ||||
15. Round | 22/11/1999 | Coventry City | - | Aston Villa | 2:1 | ||||
16. Round | 27/11/1999 | Everton FC | - | Aston Villa | 0:0 | ||||
17. Round | 04/12/1999 | Aston Villa | - | Newcastle United | 0:1 | ||||
18. Round | 18/12/1999 | Aston Villa | - | Sheffield Wednesday | 2:1 | ||||
22. Round | 15/01/2000 | West Ham United | - | Aston Villa | 1:1 | ||||
24. Round | 05/02/2000 | Aston Villa | - | Watford FC | 4:0 |