| 31. Round | 05/03/1949 | Middlesbrough FC | - | Wolverhampton Wanderers | 4:4 |  |
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| 32. Round | 12/03/1949 | Bolton Wanderers | - | Middlesbrough FC | 4:1 | ||||
| 33. Round | 19/03/1949 | Middlesbrough FC | - | Huddersfield Town | 1:0 | ||||
| 35. Round | 02/04/1949 | Middlesbrough FC | - | Derby County | 1:0 | ||||
| 36. Round | 09/04/1949 | Arsenal FC | - | Middlesbrough FC | 1:1 | ||||
| 37. Round | 15/04/1949 | Newcastle United | - | Middlesbrough FC | 1:0 | ||||
| 38. Round | 16/04/1949 | Middlesbrough FC | - | Liverpool FC | 0:1 | ||||
| 40. Round | 23/04/1949 | Blackpool FC | - | Middlesbrough FC | 1:1 | ||||
| 28. Round | 27/04/1949 | Middlesbrough FC | - | Stoke City | 1:1 | ||||
| 41. Round | 30/04/1949 | Middlesbrough FC | - | Sheffield United | 3:1 | |
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| 34. Round | 02/05/1949 | Manchester United | - | Middlesbrough FC | 1:0 | ||||
| 42. Round | 07/05/1949 | Aston Villa | - | Middlesbrough FC | 1:1 |
Ireland