| 41. Ronde | 02.01.1939 | Middlesbrough FC | - | Liverpool FC | 3:0 | ||||
| 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 | ||||
| 27. Ronde | 04.02.1939 | Middlesbrough FC | - | Bolton Wanderers | 1:2 | ||||
| 33. Ronde | 18.03.1939 | Huddersfield Town | - | Middlesbrough FC | 0:1 | ||||
| 36. Ronde | 10.04.1939 | Middlesbrough FC | - | Leicester City | 3:2 | ||||
| 38. Ronde | 11.04.1939 | Leicester City | - | Middlesbrough FC | 5:3 | ||||
| 39. Ronde | 15.04.1939 | Blackpool FC | - | Middlesbrough FC | 4:0 | ||||
| 40. Ronde | 22.04.1939 | Middlesbrough FC | - | Derby County | 2:0 |
Engeland