| Arsenal FC v Aston Villa FC 11/09/1999 | £3.00 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £3.50 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £2.50 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £2.00 | |
| Chester City FC v Aston Villa FC 14/09/1999 | View match | |
| 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 |