| 8. Round | 14/09/2019 | Rotherham United | - | Bolton Wanderers | 6:1 |  |
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| 9. Round | 17/09/2019 | Bolton Wanderers | - | Oxford United | 0:0 | ||||
| 10. Round | 21/09/2019 | Bolton Wanderers | - | Sunderland AFC | 1:1 | ||||
| 11. Round | 28/09/2019 | Portsmouth FC | - | Bolton Wanderers | 1:0 | ||||
| 12. Round | 07/10/2019 | Bolton Wanderers | - | Blackpool FC | 0:0 |  |
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| 14. Round | 19/10/2019 | Bolton Wanderers | - | Rochdale AFC | 1:3 | |
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| 17. Round | 02/11/2019 | Bolton Wanderers | - | Fleetwood Town | 2:1 | ||||
| 18. Round | 16/11/2019 | Bolton Wanderers | - | Milton Keynes Dons | 1:0 | |
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| 19. Round | 23/11/2019 | Accrington Stanley | - | Bolton Wanderers | 7:1 | ||||
| 20. Round | 07/12/2019 | Bolton Wanderers | - | AFC Wimbledon | 2:2 | ||||
| 21. Round | 14/12/2019 | Peterborough United | - | Bolton Wanderers | 1:0 | ||||
| 22. Round | 21/12/2019 | Bolton Wanderers | - | Southend United | 3:2 | ||||
| 23. Round | 26/12/2019 | Sunderland AFC | - | Bolton Wanderers | 0:0 | ||||
| 24. Round | 29/12/2019 | Bolton Wanderers | - | Shrewsbury Town | 1:1 | |
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| 25. Round | 01/01/2020 | Bolton Wanderers | - | Burton Albion | 3:4 |
Belgium
France