| 1. Round | 08/08/1999 | Everton FC | - | Manchester United | 1:1 | ||||
| 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 | ||||
| 10. Round | 02/10/1999 | Everton FC | - | Coventry City | 1:1 | ||||
| 11. Round | 16/10/1999 | Arsenal FC | - | Everton FC | 4:1 | ||||
| 13. Round | 30/10/1999 | Middlesbrough FC | - | Everton FC | 2:1 | ||||
| 20. Round | 28/12/1999 | Bradford City | - | Everton FC | 0:0 |  |
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| 24. Round | 06/02/2000 | Wimbledon FC | - | Everton FC | 0:3 | ||||
| 25. Round | 12/02/2000 | Everton FC | - | Derby County | 2:1 | |
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| 28. Round | 11/03/2000 | Chelsea FC | - | Everton FC | 1:1 |  |
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| 35. Round | 15/03/2000 | Coventry City | - | Everton FC | 1:0 | ||||
| 29. Round | 19/03/2000 | Everton FC | - | Newcastle United | 0:2 | ||||
| 30. Round | 25/03/2000 | Sunderland AFC | - | Everton FC | 2:1 | ||||
| 32. Round | 08/04/2000 | Leicester City | - | Everton FC | 1:1 | ||||
| 37. Round | 08/05/2000 | Leeds United | - | Everton FC | 1:1 |
England
Jamaica