| 14. Round | 17/10/1953 | Chelsea FC | - | Middlesbrough FC | 1:1 | ||||
| 16. Round | 31/10/1953 | Portsmouth FC | - | Middlesbrough FC | 0:2 | ||||
| 17. Round | 07/11/1953 | Middlesbrough FC | - | Wolverhampton Wanderers | 3:3 |  |
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| 18. Round | 14/11/1953 | Aston Villa | - | Middlesbrough FC | 5:3 | ||||
| 19. Round | 21/11/1953 | Middlesbrough FC | - | Manchester City | 0:1 | ||||
| 27. Round | 16/01/1954 | Burnley FC | - | Middlesbrough FC | 5:0 | ||||
| 31. Round | 24/02/1954 | Middlesbrough FC | - | West Bromwich Albion | 1:1 | ||||
| 32. Round | 27/02/1954 | Sheffield United | - | Middlesbrough FC | 2:2 | ||||
| 42. Round | 24/04/1954 | Arsenal FC | - | Middlesbrough FC | 3:1 |
Ireland