2. Ronde | 14.09.1938 | Liverpool FC | - | Middlesbrough FC | 3:1 | ||||
16. Ronde | 26.11.1938 | Middlesbrough FC | - | Arsenal FC | 1:1 | ||||
24. Ronde | 14.01.1939 | Chelsea FC | - | Middlesbrough FC | 4:2 | ||||
25. Ronde | 25.01.1939 | Middlesbrough FC | - | Preston North End | 2:2 | ||||
26. Ronde | 28.01.1939 | Charlton Athletic | - | Middlesbrough FC | 3:0 | ||||
40. Ronde | 22.04.1939 | Middlesbrough FC | - | Derby County | 2:0 |