| Aston Villa FC v Bradford City FC 18/09/1999 | £2.50 | |
| Aston Villa FC v Chester City FC 21/09/1999 | View match | |
| Leicester City FC v Aston Villa FC 25/09/1999 | View match | |
| Aston Villa FC v Liverpool FC 02/10/1999 | View match | |
| Aston Villa FC v Manchester United FC 13/10/1999 | View match | |
| Sunderland FC v Aston Villa FC 18/10/1999 | View match | |
| Aston Villa FC v Wimbledon 23/10/1999 | £3.00 | |
| Manchester United FC v Aston Villa FC 30/10/1999 | View match | |
| Aston Villa FC v Southampton FC 06/11/1999 | View match | |
| Coventry City FC v Aston Villa FC 22/11/1999 | View match | |
| Everton FC v Aston Villa FC 27/11/1999 | View match | |
| Aston Villa FC v Southampton FC 01/12/1999 | View match |