| 1. Round | 08/09/1888 | Bolton Wanderers | - | Derby County | 3:6 | ||||
| 1. Round | 15/09/1888 | Derby County | - | West Bromwich Albion | 1:2 | ||||
| 1. Round | 22/09/1888 | Derby County | - | Accrington FC | 1:1 | ||||
| 1. Round | 29/09/1888 | Derby County | - | Preston North End | 2:3 | ||||
| 2. Round | 06/10/1888 | West Bromwich Albion | - | Derby County | 5:0 | ||||
| 2. Round | 13/10/1888 | Accrington FC | - | Derby County | 6:2 | ||||
| 2. Round | 27/10/1888 | Everton FC | - | Derby County | 6:2 | ||||
| 3. Round | 03/11/1888 | Wolverhampton Wanderers | - | Derby County | 4:1 | ||||
| 3. Round | 24/11/1888 | Derby County | - | Blackburn Rovers | 0:2 | ||||
| 4. Round | 08/12/1888 | Preston North End | - | Derby County | 5:0 | ||||
| 4. Round | 22/12/1888 | Derby County | - | Notts County | 3:2 | ||||
| 4. Round | 26/12/1888 | Derby County | - | Bolton Wanderers | 2:3 | ||||
| 4. Round | 29/12/1888 | Aston Villa | - | Derby County | 4:2 | ||||
| 5. Round | 12/01/1889 | Derby County | - | Wolverhampton Wanderers | 3:0 | ||||
| 5. Round | 19/01/1889 | Burnley FC | - | Derby County | 1:0 | ||||
| 5. Round | 26/01/1889 | Derby County | - | Stoke City | 2:1 |
England