1. Round | 03/08/2019 | Leyton Orient | - | Cheltenham Town | 1:0 | ||||
2. Round | 10/08/2019 | Cheltenham Town | - | Scunthorpe United | 4:1 | ||||
4. Round | 20/08/2019 | Cheltenham Town | - | Carlisle United | 2:0 | ||||
5. Round | 24/08/2019 | Cheltenham Town | - | Swindon Town | 2:2 | ||||
6. Round | 31/08/2019 | Crawley Town | - | Cheltenham Town | 1:0 | ||||
24. Round | 29/12/2019 | Northampton Town | - | Cheltenham Town | 1:1 | ||||
25. Round | 01/01/2020 | Newport County | - | Cheltenham Town | 1:1 | ||||
26. Round | 04/01/2020 | Cheltenham Town | - | Oldham Athletic | 3:0 | ||||
27. Round | 11/01/2020 | Cheltenham Town | - | Walsall FC | 3:1 | ||||
28. Round | 18/01/2020 | Crewe Alexandra | - | Cheltenham Town | 1:0 | ||||
30. Round | 28/01/2020 | Bradford City | - | Cheltenham Town | 1:1 |