| 10. Ronde | 15.10.1938 | Middlesbrough FC | - | Grimsby Town | 3:2 | ||||
| 11. Ronde | 22.10.1938 | Sunderland AFC | - | Middlesbrough FC | 1:2 | ||||
| 12. Ronde | 29.10.1938 | Middlesbrough FC | - | Wolverhampton Wanderers | 1:0 | ||||
| 13. Ronde | 05.11.1938 | Everton FC | - | Middlesbrough FC | 4:0 | ||||
| 14. Ronde | 12.11.1938 | Middlesbrough FC | - | Huddersfield Town | 4:1 | ||||
| 15. Ronde | 19.11.1938 | Portsmouth FC | - | Middlesbrough FC | 1:1 | ||||
| 16. Ronde | 26.11.1938 | Middlesbrough FC | - | Arsenal FC | 1:1 | ||||
| 17. Ronde | 03.12.1938 | Brentford FC | - | Middlesbrough FC | 2:1 | ||||
| 24. Ronde | 14.01.1939 | Chelsea FC | - | Middlesbrough FC | 4:2 |
Engeland