| 3. Round | 04/11/1889 | West Bromwich Albion | - | Bolton Wanderers | 6:3 | ||||
| 3. Round | 09/11/1889 | Bolton Wanderers | - | Blackburn Rovers | 3:2 | ||||
| 3. Round | 16/11/1889 | Bolton Wanderers | - | Aston Villa | 2:0 | ||||
| 3. Round | 23/11/1889 | Preston North End | - | Bolton Wanderers | 3:1 | ||||
| 3. Round | 30/11/1889 | Bolton Wanderers | - | Derby County | 7:1 |  |
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| 4. Round | 07/12/1889 | Bolton Wanderers | - | West Bromwich Albion | 7:0 | |
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| 4. Round | 21/12/1889 | Blackburn Rovers | - | Bolton Wanderers | 7:1 | |
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| 4. Round | 26/12/1889 | Derby County | - | Bolton Wanderers | 3:2 | ||||
| 5. Round | 04/01/1890 | Accrington FC | - | Bolton Wanderers | 3:1 | |
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| 5. Round | 11/01/1890 | Notts County | - | Bolton Wanderers | 3:5 | |
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| 5. Round | 25/01/1890 | Aston Villa | - | Bolton Wanderers | 1:2 | |
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| 6. Round | 08/02/1890 | Bolton Wanderers | - | Stoke City | 5:0 | |
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| 7. Round | 01/03/1890 | Burnley FC | - | Bolton Wanderers | 7:0 | ||||
| 7. Round | 15/03/1890 | Wolverhampton Wanderers | - | Bolton Wanderers | 5:1 | |
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| 7. Round | 17/03/1890 | Bolton Wanderers | - | Burnley FC | 2:2 |
Scotland