1. Round | 08/08/1999 | Everton FC | - | Manchester United | 1:1 | ||||
7. Round | 11/09/1999 | Sheffield Wednesday | - | Everton FC | 0:2 | ||||
12. Round | 24/10/1999 | Everton FC | - | Leeds United | 4:4 | ||||
18. Round | 18/12/1999 | Watford FC | - | Everton FC | 1:3 | ||||
21. Round | 03/01/2000 | Everton FC | - | Leicester City | 2:2 | ||||
22. Round | 15/01/2000 | Everton FC | - | Tottenham Hotspur | 2:2 |