| 5. Round | 25/08/2018 | Gillingham FC | - | Coventry City | 1:1 | ||||
| 6. Round | 01/09/2018 | Coventry City | - | Rochdale AFC | 0:1 | ||||
| 7. Round | 09/09/2018 | Oxford United | - | Coventry City | 1:2 | ||||
| 18. Round | 17/11/2018 | Burton Albion | - | Coventry City | 1:0 | ||||
| 19. Round | 23/11/2018 | Coventry City | - | Peterborough United | 1:1 | ||||
| 20. Round | 27/11/2018 | Fleetwood Town | - | Coventry City | 3:0 | ||||
| 22. Round | 15/12/2018 | Coventry City | - | Luton Town | 1:2 | ||||
| 28. Round | 12/01/2019 | Coventry City | - | AFC Wimbledon | 1:1 | ||||
| 29. Round | 19/01/2019 | Plymouth Argyle | - | Coventry City | 2:1 | ||||
| 36. Round | 08/03/2019 | Coventry City | - | Burton Albion | 1:2 | ||||
| 37. Round | 12/03/2019 | Coventry City | - | Fleetwood Town | 2:1 |
Scotland