| Exeter City FC v Everton FC 11/12/1999 | View match | |
| Watford FC v Everton FC 18/12/1999 | View match | |
| Everton FC v Exeter City FC 21/12/1999 | View match | |
| Everton FC v Sunderland FC 26/12/1999 | View match | |
| Bradford City FC v Everton FC 28/12/1999 | View match | |
| Everton FC v Leicester City FC 03/01/2000 | View match | |
| Everton FC v Birmingham City FC 08/01/2000 | View match | |
| Everton FC v Tottenham Hotspur FC 15/01/2000 | £4.50 | |
| Everton FC v Tottenham Hotspur FC 15/01/2000 | £3.00 | |
| Southampton FC v Everton FC 22/01/2000 | View match | |
| Everton FC v Preston North End FC 29/01/2000 | View match | |
| Wimbledon v Everton FC 06/02/2000 | View match |