| 6. Round | 17/09/1927 | Middlesbrough FC | - | Blackburn Rovers | 2:0 | ||||
| 7. Round | 24/09/1927 | Bolton Wanderers | - | Middlesbrough FC | 0:0 | ||||
| 8. Round | 01/10/1927 | Middlesbrough FC | - | The Wednesday FC | 3:3 | ||||
| 19. Round | 17/12/1927 | Middlesbrough FC | - | Derby County | 3:3 | ||||
| 22. Round | 27/12/1927 | Newcastle United | - | Middlesbrough FC | 3:3 | ||||
| 23. Round | 31/12/1927 | Middlesbrough FC | - | Manchester United | 1:2 | ||||
| 36. Round | 02/01/1928 | Middlesbrough FC | - | Huddersfield Town | 3:1 | ||||
| 24. Round | 07/01/1928 | Everton FC | - | Middlesbrough FC | 3:1 |
England