| 1. Round | 09/08/2008 | Swindon Town | - | Tranmere Rovers | 3:1 | ||||
| 2. Round | 16/08/2008 | Cheltenham Town | - | Swindon Town | 2:0 |  |
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| 3. Round | 23/08/2008 | Swindon Town | - | Colchester United | 1:3 | ||||
| 4. Round | 30/08/2008 | Milton Keynes Dons | - | Swindon Town | 1:2 | ||||
| 5. Round | 05/09/2008 | Hereford United | - | Swindon Town | 1:1 | ||||
| 6. Round | 13/09/2008 | Swindon Town | - | Leeds United | 1:3 | ||||
| 7. Round | 20/09/2008 | Stockport County | - | Swindon Town | 1:1 | |
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| 8. Round | 28/09/2008 | Swindon Town | - | Millwall FC | 1:2 | ||||
| 11. Round | 18/10/2008 | Southend United | - | Swindon Town | 2:1 | ||||
| 12. Round | 21/10/2008 | Swindon Town | - | Northampton Town | 2:1 | ||||
| 13. Round | 25/10/2008 | Swindon Town | - | Oldham Athletic | 2:0 | ||||
| 15. Round | 01/11/2008 | Scunthorpe United | - | Swindon Town | 3:3 | |
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| 17. Round | 22/11/2008 | Bristol Rovers | - | Swindon Town | 2:2 | ||||
| 18. Round | 25/11/2008 | Swindon Town | - | Peterborough United | 2:2 | ||||
| 14. Round | 29/11/2008 | Walsall FC | - | Swindon Town | 2:1 | ||||
| 19. Round | 06/12/2008 | Swindon Town | - | Carlisle United | 1:1 | |
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| 20. Round | 13/12/2008 | Crewe Alexandra | - | Swindon Town | 1:0 | ||||
| 21. Round | 20/12/2008 | Swindon Town | - | Yeovil Town | 2:3 |
England