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 | ||||
4. Round | 19/09/1908 | Middlesbrough FC | - | Everton FC | 2:3 | ||||
5. Round | 26/09/1908 | Leicester Fosse | - | Middlesbrough FC | 1:1 | ||||
6. Round | 03/10/1908 | Middlesbrough FC | - | Woolwich Arsenal | 1:1 | ||||
8. Round | 17/10/1908 | Middlesbrough FC | - | Newcastle United | 0:0 | ||||
9. Round | 24/10/1908 | Bristol City | - | Middlesbrough FC | 1:1 | ||||
12. Round | 14/11/1908 | Manchester City | - | Middlesbrough FC | 0:0 | ||||
13. Round | 21/11/1908 | Middlesbrough FC | - | Liverpool FC | 1:0 | ||||
14. Round | 28/11/1908 | Bury FC | - | Middlesbrough FC | 2:1 | ||||
15. Round | 05/12/1908 | Middlesbrough FC | - | Sheffield United | 1:2 | ||||
16. Round | 12/12/1908 | Aston Villa | - | Middlesbrough FC | 0:3 | ||||
17. Round | 19/12/1908 | Middlesbrough FC | - | Nottingham Forest | 4:0 | ||||
33. Round | 25/12/1908 | Blackburn Rovers | - | Middlesbrough FC | 0:0 | ||||
36. Round | 26/12/1908 | Sunderland AFC | - | Middlesbrough FC | 2:0 | ||||
18. Round | 01/01/1909 | Middlesbrough FC | - | Chelsea FC | 1:4 |