| 1. Round | 30/08/1919 | Bolton Wanderers | - | Bradford Park Avenue | 1:2 | ||||
| 9. Round | 11/10/1919 | West Bromwich Albion | - | Bolton Wanderers | 4:1 | ||||
| 13. Round | 08/11/1919 | Arsenal FC | - | Bolton Wanderers | 2:2 | ||||
| 27. Round | 07/02/1920 | Bolton Wanderers | - | Chelsea FC | 1:2 | ||||
| 30. Round | 28/02/1920 | Newcastle United | - | Bolton Wanderers | 0:1 | ||||
| 32. Round | 13/03/1920 | Bolton Wanderers | - | Aston Villa | 2:1 | ||||
| 33. Round | 20/03/1920 | Oldham Athletic | - | Bolton Wanderers | 2:0 | ||||
| 34. Round | 27/03/1920 | Bolton Wanderers | - | Oldham Athletic | 1:0 | ||||
| 36. Round | 03/04/1920 | Manchester United | - | Bolton Wanderers | 1:1 | ||||
| 37. Round | 05/04/1920 | The Wednesday FC | - | Bolton Wanderers | 0:2 | ||||
| 31. Round | 07/04/1920 | Aston Villa | - | Bolton Wanderers | 3:6 | ||||
| 38. Round | 10/04/1920 | Bolton Wanderers | - | Manchester United | 3:5 | ||||
| 39. Round | 17/04/1920 | Sheffield United | - | Bolton Wanderers | 3:2 |
England