| 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 | |
| Aston Villa FC v Newcastle United FC 04/12/1999 | View match | |
| Aston Villa FC v Darlington FC 11/12/1999 | View match | |
| Aston Villa FC v Sheffield Wednesday FC 18/12/1999 | View match | |
| Derby County FC v Aston Villa FC 26/12/1999 | View match | |
| Aston Villa FC v Tottenham Hotspur FC 29/12/1999 | £4.50 | |
| Leeds United FC v Aston Villa FC 03/01/2000 | View match |