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 | ||||
7. Round | 11/09/1999 | Sheffield Wednesday | - | Everton FC | 0:2 | ||||
26. Round | 26/02/2000 | West Ham United | - | Everton FC | 0:4 | ||||
27. Round | 04/03/2000 | Everton FC | - | Sheffield Wednesday | 1:1 | ||||
34. Round | 21/04/2000 | Everton FC | - | Liverpool FC | 0:0 | ||||
37. Round | 08/05/2000 | Leeds United | - | Everton FC | 1:1 |