| 27. Round | 05/01/2019 | Crawley Town | - | Cheltenham Town | 1:0 | ||||
| 28. Round | 12/01/2019 | Cheltenham Town | - | Tranmere Rovers | 1:3 | ||||
| 30. Round | 26/01/2019 | Cheltenham Town | - | Macclesfield Town | 3:2 | ||||
| 33. Round | 16/02/2019 | Grimsby Town | - | Cheltenham Town | 1:0 | ||||
| 37. Round | 05/03/2019 | Cheltenham Town | - | Bury FC | 1:1 |  |
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| 44. Round | 22/04/2019 | Morecambe FC | - | Cheltenham Town | 4:0 | ||||
| 45. Round | 27/04/2019 | Cheltenham Town | - | Swindon Town | 3:2 | ||||
| 46. Round | 04/05/2019 | Stevenage FC | - | Cheltenham Town | 2:0 |
England