1. Round | 08/08/1999 | Everton FC | - | Manchester United | 1:1 | ||||
2. Round | 11/08/1999 | Aston Villa | - | Everton FC | 3:0 | ||||
3. Round | 14/08/1999 | Tottenham Hotspur | - | Everton FC | 3:2 | ||||
4. Round | 21/08/1999 | Everton FC | - | Southampton FC | 4:1 | ||||
5. Round | 25/08/1999 | Everton FC | - | Wimbledon FC | 4:0 | ||||
6. Round | 28/08/1999 | Derby County | - | Everton FC | 1:0 | ||||
7. Round | 11/09/1999 | Sheffield Wednesday | - | Everton FC | 0:2 | ||||
8. Round | 19/09/1999 | Everton FC | - | West Ham United | 1:0 | ||||
10. Round | 02/10/1999 | Everton FC | - | Coventry City | 1:1 | ||||
11. Round | 16/10/1999 | Arsenal FC | - | Everton FC | 4:1 | ||||
12. Round | 24/10/1999 | Everton FC | - | Leeds United | 4:4 | ||||
20. Round | 28/12/1999 | Bradford City | - | Everton FC | 0:0 | ||||
21. Round | 03/01/2000 | Everton FC | - | Leicester City | 2:2 | ||||
35. Round | 15/03/2000 | Coventry City | - | Everton FC | 1:0 |