| 31. Round | 27/03/1909 | Manchester City | - | The Wednesday FC | 4:0 | ||||
| 24. Round | 29/03/1909 | The Wednesday FC | - | Sunderland AFC | 2:5 | ||||
| 32. Round | 03/04/1909 | The Wednesday FC | - | Manchester United | 2:0 | ||||
| 34. Round | 10/04/1909 | Liverpool FC | - | The Wednesday FC | 1:2 |  |
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| 35. Round | 12/04/1909 | Woolwich Arsenal | - | The Wednesday FC | 2:0 | ||||
| 37. Round | 17/04/1909 | The Wednesday FC | - | Everton FC | 2:0 | ||||
| 28. Round | 19/04/1909 | The Wednesday FC | - | Blackburn Rovers | 1:2 | ||||
| 38. Round | 24/04/1909 | Bury FC | - | The Wednesday FC | 4:2 |
Northern Ireland
All Ireland