13. Round | 15/10/1949 | Middlesbrough FC | - | Arsenal FC | 1:1 | ||||
14. Round | 22/10/1949 | Bolton Wanderers | - | Middlesbrough FC | 1:2 | ![]() |
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15. Round | 29/10/1949 | Middlesbrough FC | - | Birmingham City | 1:0 | ![]() |
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16. Round | 05/11/1949 | Derby County | - | Middlesbrough FC | 1:0 | ||||
17. Round | 12/11/1949 | Middlesbrough FC | - | West Bromwich Albion | 3:0 | ![]() |
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29. Round | 04/02/1950 | Middlesbrough FC | - | Charlton Athletic | 1:0 | ![]() |
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30. Round | 18/02/1950 | Manchester City | - | Middlesbrough FC | 0:1 | ![]() |
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31. Round | 25/02/1950 | Middlesbrough FC | - | Liverpool FC | 4:1 | ||||
32. Round | 08/03/1950 | Arsenal FC | - | Middlesbrough FC | 1:1 | ||||
33. Round | 11/03/1950 | Middlesbrough FC | - | Manchester United | 2:3 | ![]() |
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35. Round | 25/03/1950 | Middlesbrough FC | - | Derby County | 3:1 | ||||
34. Round | 29/03/1950 | Chelsea FC | - | Middlesbrough FC | 2:1 |