| 1. Round | 20/08/1949 | Middlesbrough FC | - | Everton FC | 0:1 | ||||
| 2. Round | 24/08/1949 | Everton FC | - | Newcastle United | 2:1 |  |
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| 3. Round | 27/08/1949 | Everton FC | - | Liverpool FC | 0:0 | ||||
| 4. Round | 31/08/1949 | Newcastle United | - | Everton FC | 4:0 | ||||
| 5. Round | 03/09/1949 | Everton FC | - | Huddersfield Town | 3:0 | ||||
| 9. Round | 17/09/1949 | Everton FC | - | Wolverhampton Wanderers | 1:2 | ||||
| 10. Round | 24/09/1949 | Aston Villa | - | Everton FC | 2:2 | ||||
| 11. Round | 01/10/1949 | Everton FC | - | Charlton Athletic | 0:1 | ||||
| 12. Round | 08/10/1949 | Arsenal FC | - | Everton FC | 5:2 | |
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| 14. Round | 22/10/1949 | Birmingham City | - | Everton FC | 0:0 | ||||
| 15. Round | 29/10/1949 | Everton FC | - | Derby County | 1:2 | ||||
| 16. Round | 05/11/1949 | West Bromwich Albion | - | Everton FC | 4:0 | ||||
| 17. Round | 12/11/1949 | Everton FC | - | Manchester United | 0:0 | ||||
| 18. Round | 19/11/1949 | Chelsea FC | - | Everton FC | 3:2 | ||||
| 19. Round | 26/11/1949 | Everton FC | - | Stoke City | 2:1 | |
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| 20. Round | 03/12/1949 | Burnley FC | - | Everton FC | 5:1 | ||||
| 21. Round | 10/12/1949 | Everton FC | - | Sunderland AFC | 0:2 |
Scotland