| 13. Round | 05/02/2019 | Cheltenham Town | - | Yeovil Town | 1:0 |  |
|||
| 32. Round | 09/02/2019 | Colchester United | - | Cheltenham Town | 3:0 | ||||
| 33. Round | 16/02/2019 | Grimsby Town | - | Cheltenham Town | 1:0 | ||||
| 31. Round | 19/02/2019 | Cheltenham Town | - | Cambridge United | 2:0 | ||||
| 36. Round | 09/03/2019 | Cheltenham Town | - | Notts County | 4:1 | ||||
| 38. Round | 15/03/2019 | Newport County | - | Cheltenham Town | 1:0 | ||||
| 39. Round | 23/03/2019 | Cheltenham Town | - | Northampton Town | 3:1 | ||||
| 41. Round | 06/04/2019 | Cheltenham Town | - | Exeter City | 1:1 | ||||
| 42. Round | 13/04/2019 | Lincoln City | - | Cheltenham Town | 1:1 | ||||
| 44. Round | 22/04/2019 | Morecambe FC | - | Cheltenham Town | 4:0 | |
England