1. Round | 03/08/2019 | Leyton Orient | - | Cheltenham Town | 1:0 | ||||
2. Round | 10/08/2019 | Cheltenham Town | - | Scunthorpe United | 4:1 | ||||
3. Round | 17/08/2019 | Morecambe FC | - | Cheltenham Town | 0:0 | ||||
4. Round | 20/08/2019 | Cheltenham Town | - | Carlisle United | 2:0 | ||||
5. Round | 24/08/2019 | Cheltenham Town | - | Swindon Town | 2:2 | ||||
21. Round | 14/12/2019 | Cheltenham Town | - | Cambridge United | 1:1 | ||||
22. Round | 21/12/2019 | Port Vale FC | - | Cheltenham Town | 1:1 |