| 9. Round | 20/09/1952 | Liverpool FC | - | Middlesbrough FC | 4:1 | ||||
| 15. Round | 01/11/1952 | Middlesbrough FC | - | Charlton Athletic | 1:0 | ||||
| 16. Round | 08/11/1952 | Arsenal FC | - | Middlesbrough FC | 2:1 | ||||
| 17. Round | 15/11/1952 | Middlesbrough FC | - | Derby County | 1:0 | ||||
| 28. Round | 07/02/1953 | Middlesbrough FC | - | Liverpool FC | 2:3 | ||||
| 29. Round | 18/02/1953 | Bolton Wanderers | - | Middlesbrough FC | 5:3 |  |
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| 30. Round | 21/02/1953 | West Bromwich Albion | - | Middlesbrough FC | 3:0 | ||||
| 31. Round | 04/03/1953 | Middlesbrough FC | - | Aston Villa | 1:0 | ||||
| 32. Round | 07/03/1953 | Sunderland AFC | - | Middlesbrough FC | 1:1 |
England