| 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 | ||||
| 19. Round | 07/09/1909 | Bolton Wanderers | - | Newcastle United | 0:4 | ||||
| 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 | ||||
| 16. Round | 11/12/1909 | Tottenham Hotspur | - | Bolton Wanderers | 1:1 | ||||
| 17. Round | 18/12/1909 | Bolton Wanderers | - | Preston North End | 3:1 | ||||
| 31. Round | 25/12/1909 | Liverpool FC | - | Bolton Wanderers | 3:0 | ||||
| 20. Round | 01/01/1910 | Bolton Wanderers | - | Notts County | 3:4 | ||||
| 13. Round | 03/01/1910 | Bolton Wanderers | - | The Wednesday FC | 0:2 | ||||
| 21. Round | 08/01/1910 | Aston Villa | - | Bolton Wanderers | 3:1 |
England