| Aston Villa FC v Charlton Athletic FC 08/05/1999 | View match | |
| Arsenal FC v Aston Villa FC 16/05/1999 | £2.50 | |
| Arsenal FC v Aston Villa FC 16/05/1999 | £3.50 | |
| Newcastle United FC v Aston Villa FC 07/08/1999 | View match | |
| Aston Villa FC v Everton FC 11/08/1999 | £2.00 | |
| Aston Villa FC v West Ham United FC 16/08/1999 | £3.50 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £3.00 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £4.00 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £3.50 | |
| Chelsea FC v Aston Villa FC 21/08/1999 | £2.50 | |
| Watford FC v Aston Villa FC 24/08/1999 | View match | |
| Aston Villa FC v Middlesbrough FC 28/08/1999 | £2.50 |