11. Round | 07/11/1908 | The Wednesday FC | - | Middlesbrough FC | 3:2 | ||||
12. Round | 14/11/1908 | Manchester City | - | Middlesbrough FC | 0:0 | ||||
24. Round | 17/03/1909 | Woolwich Arsenal | - | Middlesbrough FC | 1:1 | ||||
30. Round | 20/03/1909 | Middlesbrough FC | - | Manchester City | 3:0 | ||||
32. Round | 03/04/1909 | Middlesbrough FC | - | Bury FC | 0:1 | ||||
34. Round | 10/04/1909 | Sheffield United | - | Middlesbrough FC | 2:0 |