| Aston Villa FC v Everton FC 11/08/1999 | £2.00 | |
| Tottenham Hotspur FC v Everton FC 14/08/1999 | £5.00 | |
| Sheffield Wednesday FC v Everton FC 11/09/1999 | £9.50 | |
| Everton FC v West Ham United FC 19/09/1999 | £5.00 | |
| Arsenal FC v Everton FC 16/10/1999 | £3.50 | |
| Arsenal FC v Everton FC 16/10/1999 | £2.00 | |
| Arsenal FC v Everton FC 16/10/1999 | £4.00 | |
| Everton FC v Chelsea FC 20/11/1999 | £3.50 | |
| Everton FC v Tottenham Hotspur FC 15/01/2000 | £3.00 | |
| Everton FC v Tottenham Hotspur FC 15/01/2000 | £4.50 | |
| West Ham United FC v Everton FC 26/02/2000 | £5.00 | |
| Chelsea FC v Everton FC 11/03/2000 | £3.00 |