8. Round | 16/10/1909 | Tottenham Hotspur | - | Middlesbrough FC | 1:3 | ||||
9. Round | 23/10/1909 | Middlesbrough FC | - | Blackburn Rovers | 1:3 | ||||
16. Round | 11/12/1909 | Liverpool FC | - | Middlesbrough FC | 0:0 | ||||
18. Round | 25/12/1909 | Middlesbrough FC | - | Bradford City | 3:7 | ||||
19. Round | 27/12/1909 | Bradford City | - | Middlesbrough FC | 4:1 | ||||
31. Round | 01/01/1910 | Sheffield United | - | Middlesbrough FC | 2:0 |