| 2. Journée | 05.09.1908 | Middlesbrough FC | - | Bradford City | 1:0 | ||||
| 1. Journée | 09.09.1908 | Middlesbrough FC | - | Sunderland AFC | 0:3 | ||||
| 3. Journée | 12.09.1908 | Manchester United | - | Middlesbrough FC | 6:3 | ||||
| 5. Journée | 26.09.1908 | Leicester Fosse | - | Middlesbrough FC | 1:1 | ||||
| 23. Journée | 30.01.1909 | Middlesbrough FC | - | Leicester Fosse | 6:2 | ||||
| 25. Journée | 13.02.1909 | Middlesbrough FC | - | Notts County | 1:2 | ||||
| 26. Journée | 31.03.1909 | Newcastle United | - | Middlesbrough FC | 1:0 | ||||
| 32. Journée | 03.04.1909 | Middlesbrough FC | - | Bury FC | 0:1 | ||||
| 19. Journée | 09.04.1909 | Chelsea FC | - | Middlesbrough FC | 3:0 | ||||
| 34. Journée | 10.04.1909 | Sheffield United | - | Middlesbrough FC | 2:0 | ||||
| 35. Journée | 12.04.1909 | Middlesbrough FC | - | Blackburn Rovers | 1:0 | ||||
| 38. Journée | 24.04.1909 | Nottingham Forest | - | Middlesbrough FC | 4:1 |
Angleterre