| Chelsea FC v Aston Villa FC 21/08/1999 | £3.00 | |
| Aston Villa FC v Middlesbrough FC 28/08/1999 | £2.50 | |
| Arsenal FC v Aston Villa FC 11/09/1999 | £2.00 | |
| 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 | £3.00 | |
| Aston Villa FC v Bradford City FC 18/09/1999 | £2.50 | |
| Aston Villa FC v Wimbledon 23/10/1999 | £3.00 | |
| Aston Villa FC v Tottenham Hotspur FC 29/12/1999 | £4.50 | |
| West Ham United FC v Aston Villa FC 11/01/2000 | £5.00 | |
| West Ham United FC v Aston Villa FC 15/01/2000 | £5.00 | |
| Aston Villa FC v Arsenal FC 05/03/2000 | £2.50 |