| 18. Round | 01/09/1909 | Newcastle United | - | Bolton Wanderers | 1:0 | ||||
| 2. Round | 04/09/1909 | Bolton Wanderers | - | Aston Villa | 1:2 | ||||
| 1. Round | 06/09/1909 | Bolton Wanderers | - | Liverpool FC | 1:2 | ||||
| 3. Round | 11/09/1909 | Sheffield United | - | Bolton Wanderers | 2:2 | ||||
| 9. Round | 23/10/1909 | Bolton Wanderers | - | Sunderland AFC | 2:1 | ||||
| 10. Round | 30/10/1909 | Everton FC | - | Bolton Wanderers | 3:1 | ||||
| 11. Round | 06/11/1909 | Bolton Wanderers | - | Manchester United | 2:3 | ||||
| 12. Round | 13/11/1909 | Bradford City | - | Bolton Wanderers | 1:0 | ||||
| 14. Round | 27/11/1909 | Bristol City | - | Bolton Wanderers | 1:0 | ||||
| 15. Round | 04/12/1909 | Bolton Wanderers | - | Bury FC | 1:3 |
England