| 1. Round | 28/09/1895 | Small Heath Birmingham | - | Bolton Wanderers | 1:2 | ||||
| 2. Round | 05/10/1895 | Bolton Wanderers | - | Bury FC | 2:4 | ||||
| 3. Round | 30/11/1895 | Bolton Wanderers | - | Blackburn Rovers | 1:1 | ||||
| 4. Round | 07/12/1895 | Blackburn Rovers | - | Bolton Wanderers | 3:2 | ||||
| 4. Round | 14/12/1895 | Aston Villa | - | Bolton Wanderers | 2:0 | ||||
| 4. Round | 21/12/1895 | Bolton Wanderers | - | Sunderland AFC | 1:0 | ||||
| 4. Round | 26/12/1895 | Derby County | - | Bolton Wanderers | 2:1 |  |
|||
| 6. Round | 22/02/1896 | Bolton Wanderers | - | Small Heath Birmingham | 4:1 | ||||
| 7. Round | 07/03/1896 | Bolton Wanderers | - | Aston Villa | 2:2 | ||||
| 7. Round | 14/03/1896 | Bolton Wanderers | - | Preston North End | 1:0 | |
|||
| 8. Round | 03/04/1896 | Bolton Wanderers | - | Sheffield United | 4:1 | |
|||
| 8. Round | 04/04/1896 | Bolton Wanderers | - | West Bromwich Albion | 2:1 | |
|||
| 8. Round | 06/04/1896 | Everton FC | - | Bolton Wanderers | 1:1 | ||||
| 8. Round | 11/04/1896 | Wolverhampton Wanderers | - | Bolton Wanderers | 5:0 | ||||
| 8. Round | 25/04/1896 | Bolton Wanderers | - | The Wednesday FC | 2:0 | |
Scotland