| 1. Round | 01/09/1900 | Manchester City | - | The Wednesday FC | 2:2 | ||||
| 3. Round | 15/09/1900 | Bury FC | - | The Wednesday FC | 2:0 | ||||
| 5. Round | 29/09/1900 | Nottingham Forest | - | The Wednesday FC | 1:0 | ||||
| 12. Round | 17/11/1900 | The Wednesday FC | - | Liverpool FC | 3:2 | ||||
| 13. Round | 24/11/1900 | Everton FC | - | The Wednesday FC | 1:1 | ||||
| 14. Round | 01/12/1900 | The Wednesday FC | - | Newcastle United | 2:2 | ||||
| 15. Round | 08/12/1900 | Sunderland AFC | - | The Wednesday FC | 1:0 | ||||
| 16. Round | 15/12/1900 | Sheffield United | - | The Wednesday FC | 1:0 | ||||
| 24. Round | 16/02/1901 | The Wednesday FC | - | Blackburn Rovers | 1:1 |
Scotland