1. Round | 27/08/1938 | Middlesbrough FC | - | Manchester United | 3:1 | ||||
4. Round | 31/08/1938 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
3. Round | 03/09/1938 | Stoke City | - | Middlesbrough FC | 1:3 | ||||
5. Round | 10/09/1938 | Middlesbrough FC | - | Chelsea FC | 1:1 | ||||
18. Round | 10/12/1938 | Middlesbrough FC | - | Blackpool FC | 9:2 | ||||
19. Round | 17/12/1938 | Derby County | - | Middlesbrough FC | 1:4 | ||||
20. Round | 24/12/1938 | Manchester United | - | Middlesbrough FC | 1:1 | ||||
21. Round | 26/12/1938 | Birmingham FC | - | Middlesbrough FC | 2:1 | ||||
22. Round | 27/12/1938 | Middlesbrough FC | - | Birmingham FC | 2:2 | ||||
23. Round | 31/12/1938 | Middlesbrough FC | - | Stoke City | 5:1 | ||||
41. Round | 02/01/1939 | Middlesbrough FC | - | Liverpool FC | 3:0 | ||||
25. Round | 25/01/1939 | Middlesbrough FC | - | Preston North End | 2:2 | ||||
26. Round | 28/01/1939 | Charlton Athletic | - | Middlesbrough FC | 3:0 | ||||
39. Round | 15/04/1939 | Blackpool FC | - | Middlesbrough FC | 4:0 | ||||
40. Round | 22/04/1939 | Middlesbrough FC | - | Derby County | 2:0 | ||||
42. Round | 06/05/1939 | Aston Villa | - | Middlesbrough FC | 1:1 |