| 2. Journée | 16.08.2008 | Cheltenham Town | - | Swindon Town | 2:0 | ||||
| 3. Journée | 23.08.2008 | Oldham Athletic | - | Cheltenham Town | 4:0 | ||||
| 5. Journée | 06.09.2008 | Cheltenham Town | - | Huddersfield Town | 1:2 |  |
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| 6. Journée | 12.09.2008 | Hartlepool United | - | Cheltenham Town | 4:1 | ||||
| 14. Journée | 16.09.2008 | Cheltenham Town | - | Bristol Rovers | 2:1 |  |
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| 7. Journée | 20.09.2008 | Millwall FC | - | Cheltenham Town | 2:0 |  |
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| 10. Journée | 11.10.2008 | Cheltenham Town | - | Colchester United | 4:3 | |
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| 19. Journée | 06.12.2008 | Cheltenham Town | - | Crewe Alexandra | 1:0 | ||||
| 20. Journée | 13.12.2008 | Leyton Orient | - | Cheltenham Town | 1:2 | |
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| 21. Journée | 20.12.2008 | Cheltenham Town | - | Walsall FC | 0:0 | ||||
| 22. Journée | 26.12.2008 | Yeovil Town | - | Cheltenham Town | 1:1 | ||||
| 23. Journée | 28.12.2008 | Cheltenham Town | - | Peterborough United | 3:6 | |
Angleterre