| 14. Round | 16/09/2008 | Cheltenham Town | - | Bristol Rovers | 2:1 |  |
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| 7. Round | 20/09/2008 | Millwall FC | - | Cheltenham Town | 2:0 | ||||
| 8. Round | 27/09/2008 | Cheltenham Town | - | Stockport County | 2:2 | ||||
| 9. Round | 04/10/2008 | Brighton & Hove Albion | - | Cheltenham Town | 3:3 |  |
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| 10. Round | 11/10/2008 | Cheltenham Town | - | Colchester United | 4:3 | ||||
| 11. Round | 18/10/2008 | Cheltenham Town | - | Scunthorpe United | 1:2 | ||||
| 13. Round | 25/10/2008 | Milton Keynes Dons | - | Cheltenham Town | 3:1 | ||||
| 15. Round | 01/11/2008 | Cheltenham Town | - | Leeds United | 0:1 | ||||
| 16. Round | 15/11/2008 | Hereford United | - | Cheltenham Town | 3:0 | ||||
| 17. Round | 22/11/2008 | Carlisle United | - | Cheltenham Town | 1:0 | ||||
| 18. Round | 25/11/2008 | Cheltenham Town | - | Southend United | 0:0 | ||||
| 19. Round | 06/12/2008 | Cheltenham Town | - | Crewe Alexandra | 1:0 | ||||
| 20. Round | 13/12/2008 | Leyton Orient | - | Cheltenham Town | 1:2 |
Scotland