| 15. Round | 22/11/1919 | Everton FC | - | Bolton Wanderers | 3:3 |  |
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| 16. Round | 29/11/1919 | Bolton Wanderers | - | Everton FC | 0:2 | ||||
| 17. Round | 06/12/1919 | Bradford City | - | Bolton Wanderers | 0:1 | ||||
| 18. Round | 13/12/1919 | Bolton Wanderers | - | Bradford City | 1:1 | ||||
| 19. Round | 20/12/1919 | Blackburn Rovers | - | Bolton Wanderers | 2:2 | ||||
| 21. Round | 26/12/1919 | Preston North End | - | Bolton Wanderers | 1:1 | ||||
| 23. Round | 03/01/1920 | Bolton Wanderers | - | Notts County | 1:0 | ||||
| 32. Round | 13/03/1920 | Bolton Wanderers | - | Aston Villa | 2:1 | ||||
| 34. Round | 27/03/1920 | Bolton Wanderers | - | Oldham Athletic | 1:0 | ||||
| 31. Round | 07/04/1920 | Aston Villa | - | Bolton Wanderers | 3:6 | ||||
| 38. Round | 10/04/1920 | Bolton Wanderers | - | Manchester United | 3:5 |
England