| 17. Round | 19/12/1908 | Manchester City | - | Aston Villa | 2:0 | ||||
| 33. Round | 25/12/1908 | Manchester City | - | Chelsea FC | 1:2 | ||||
| 1. Round | 28/12/1908 | Nottingham Forest | - | Manchester City | 0:2 | ||||
| 21. Round | 09/01/1909 | Manchester City | - | Bradford City | 4:3 | ||||
| 22. Round | 23/01/1909 | Manchester United | - | Manchester City | 3:1 | ||||
| 23. Round | 30/01/1909 | Manchester City | - | Everton FC | 4:0 |  |
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| 25. Round | 13/02/1909 | Manchester City | - | Woolwich Arsenal | 2:2 | ||||
| 26. Round | 20/02/1909 | Notts County | - | Manchester City | 5:1 | ||||
| 27. Round | 27/02/1909 | Manchester City | - | Newcastle United | 0:2 | ||||
| 24. Round | 11/03/1909 | Leicester Fosse | - | Manchester City | 3:1 | ||||
| 31. Round | 27/03/1909 | Manchester City | - | The Wednesday FC | 4:0 | ||||
| 32. Round | 03/04/1909 | Manchester City | - | Liverpool FC | 4:0 | ||||
| 19. Round | 09/04/1909 | Sunderland AFC | - | Manchester City | 2:0 | ||||
| 34. Round | 10/04/1909 | Bury FC | - | Manchester City | 1:0 | ||||
| 36. Round | 13/04/1909 | Manchester City | - | Nottingham Forest | 2:1 | ||||
| 37. Round | 17/04/1909 | Manchester City | - | Sheffield United | 1:3 | ||||
| 38. Round | 24/04/1909 | Aston Villa | - | Manchester City | 2:1 |
England