| 2. Round | 10/08/2019 | Bolton Wanderers | - | Coventry City | 0:0 | ||||
| 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 | ||||
| 12. Round | 07/10/2019 | Bolton Wanderers | - | Blackpool FC | 0:0 | ||||
| 14. Round | 19/10/2019 | Bolton Wanderers | - | Rochdale AFC | 1:3 | ||||
| 17. Round | 02/11/2019 | Bolton Wanderers | - | Fleetwood Town | 2:1 | ||||
| 19. Round | 23/11/2019 | Accrington Stanley | - | Bolton Wanderers | 7:1 | ||||
| 20. Round | 07/12/2019 | Bolton Wanderers | - | AFC Wimbledon | 2:2 | ||||
| 22. Round | 21/12/2019 | Bolton Wanderers | - | Southend United | 3:2 | ||||
| 24. Round | 29/12/2019 | Bolton Wanderers | - | Shrewsbury Town | 1:1 | ||||
| 27. Round | 11/01/2020 | Rochdale AFC | - | Bolton Wanderers | 2:0 | ||||
| 35. Round | 22/02/2020 | Milton Keynes Dons | - | Bolton Wanderers | 1:0 |
England