| 6. Round | 05/09/2003 | Cheltenham Town | - | Northampton Town | 4:3 | ||||
| 8. Round | 16/09/2003 | Cheltenham Town | - | Oxford United | 0:0 | ||||
| 9. Round | 20/09/2003 | Cheltenham Town | - | Cambridge United | 0:3 | ||||
| 10. Round | 27/09/2003 | Bristol Rovers | - | Cheltenham Town | 2:0 | ||||
| 12. Round | 04/10/2003 | Cheltenham Town | - | Yeovil Town | 3:1 | ||||
| 15. Round | 21/10/2003 | Cheltenham Town | - | Darlington FC | 2:1 | ||||
| 16. Round | 25/10/2003 | Mansfield Town | - | Cheltenham Town | 4:0 | ||||
| 17. Round | 01/11/2003 | Cheltenham Town | - | York City | 1:1 | ||||
| 18. Round | 15/11/2003 | Torquay United | - | Cheltenham Town | 3:1 |
Australia