| 1. Round | 22/09/1888 | Preston North End | - | Bolton Wanderers | 3:1 | ||||
| 1. Round | 29/09/1888 | Bolton Wanderers | - | Everton FC | 6:2 | ||||
| 2. Round | 06/10/1888 | Burnley FC | - | Bolton Wanderers | 4:1 | ||||
| 4. Round | 08/12/1888 | Blackburn Rovers | - | Bolton Wanderers | 4:4 | ||||
| 4. Round | 22/12/1888 | Bolton Wanderers | - | Accrington FC | 4:1 | ||||
| 4. Round | 26/12/1888 | Derby County | - | Bolton Wanderers | 2:3 | ||||
| 4. Round | 29/12/1888 | Bolton Wanderers | - | Wolverhampton Wanderers | 2:1 | ||||
| 5. Round | 12/01/1889 | Aston Villa | - | Bolton Wanderers | 6:2 | ||||
| 5. Round | 19/01/1889 | Stoke City | - | Bolton Wanderers | 2:2 | ||||
| 5. Round | 26/01/1889 | Bolton Wanderers | - | Blackburn Rovers | 3:2 | ||||
| 7. Round | 05/03/1889 | Notts County | - | Bolton Wanderers | 0:4 | ||||
| 7. Round | 23/03/1889 | Accrington FC | - | Bolton Wanderers | 2:3 |
Wales