| 1. Round | 03/08/2019 | Wycombe Wanderers | - | Bolton Wanderers | 2:0 | ||||
| 2. Round | 10/08/2019 | Bolton Wanderers | - | Coventry City | 0:0 |  |
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| 3. Round | 17/08/2019 | Tranmere Rovers | - | Bolton Wanderers | 5:0 | ||||
| 5. Round | 24/08/2019 | Bolton Wanderers | - | Ipswich Town | 0:5 | ||||
| 6. Round | 31/08/2019 | Gillingham FC | - | Bolton Wanderers | 5:0 | ||||
| 8. Round | 14/09/2019 | Rotherham United | - | Bolton Wanderers | 6:1 | ||||
| 9. Round | 17/09/2019 | Bolton Wanderers | - | Oxford United | 0:0 | ||||
| 25. Round | 01/01/2020 | Bolton Wanderers | - | Burton Albion | 3:4 |
England