2. Round | 05/09/1908 | Middlesbrough FC | - | Bradford City | 1:0 | ||||
1. Round | 09/09/1908 | Middlesbrough FC | - | Sunderland AFC | 0:3 | ||||
3. Round | 12/09/1908 | Manchester United | - | Middlesbrough FC | 6:3 | ||||
5. Round | 26/09/1908 | Leicester Fosse | - | 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 | ||||
26. Round | 31/03/1909 | Newcastle United | - | Middlesbrough FC | 1:0 | ||||
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 | ||||
35. Round | 12/04/1909 | Middlesbrough FC | - | Blackburn Rovers | 1:0 | ||||
38. Round | 24/04/1909 | Nottingham Forest | - | Middlesbrough FC | 4:1 |