| 18. Round | 01/09/1908 | Manchester City | - | Sunderland AFC | 1:0 | ||||
| 2. Round | 05/09/1908 | Manchester City | - | Blackburn Rovers | 3:3 | ||||
| 3. Round | 12/09/1908 | Bradford City | - | Manchester City | 0:0 | ||||
| 5. Round | 26/09/1908 | Everton FC | - | Manchester City | 6:3 | ||||
| 6. Round | 03/10/1908 | Manchester City | - | Leicester Fosse | 5:2 |  |
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| 7. Round | 10/10/1908 | Woolwich Arsenal | - | Manchester City | 3:0 | ||||
| 13. Round | 21/11/1908 | The Wednesday FC | - | Manchester City | 3:1 | ||||
| 27. Round | 27/02/1909 | Manchester City | - | Newcastle United | 0:2 |
Scotland