18. Round | 01/01/1909 | Middlesbrough FC | - | Chelsea FC | 1:4 | ||||
20. Round | 02/01/1909 | Bradford City | - | Middlesbrough FC | 0:2 | ||||
21. Round | 09/01/1909 | Middlesbrough FC | - | Manchester United | 5:0 | ||||
22. Round | 23/01/1909 | Everton FC | - | Middlesbrough FC | 1:1 | ||||
23. Round | 30/01/1909 | Middlesbrough FC | - | Leicester Fosse | 6:2 | ||||
25. Round | 13/02/1909 | Middlesbrough FC | - | Notts County | 1:2 | ||||
24. Round | 17/03/1909 | Woolwich Arsenal | - | Middlesbrough FC | 1:1 | ||||
32. Round | 03/04/1909 | Middlesbrough FC | - | Bury FC | 0:1 | ||||
19. Round | 09/04/1909 | Chelsea FC | - | Middlesbrough FC | 3:0 | ||||
34. Round | 10/04/1909 | Sheffield United | - | Middlesbrough FC | 2:0 |