| 1. Round | 08/09/1888 | Bolton Wanderers | - | Derby County | 3:6 |  |
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| 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 | ||||
| 4. Round | 22/12/1888 | Derby County | - | Notts County | 3:2 | ||||
| 4. Round | 29/12/1888 | Aston Villa | - | Derby County | 4:2 | ||||
| 5. Round | 12/01/1889 | Derby County | - | Wolverhampton Wanderers | 3:0 | |
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| 5. Round | 19/01/1889 | Burnley FC | - | Derby County | 1:0 | ||||
| 5. Round | 26/01/1889 | Derby County | - | Stoke City | 2:1 | |
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| 7. Round | 02/03/1889 | Derby County | - | Burnley FC | 1:0 | |
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| 7. Round | 09/03/1889 | Derby County | - | Aston Villa | 5:2 | |
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| 7. Round | 16/03/1889 | Notts County | - | Derby County | 3:5 | |
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| 8. Round | 06/04/1889 | Stoke City | - | Derby County | 1:1 | ||||
| 8. Round | 15/04/1889 | Blackburn Rovers | - | Derby County | 3:0 |
England