| 1. Ronde | 09.08.2008 | Scunthorpe United | - | Leeds United | 1:2 | ||||
| 2. Ronde | 16.08.2008 | Walsall FC | - | Scunthorpe United | 2:1 | ||||
| 3. Ronde | 23.08.2008 | Scunthorpe United | - | Peterborough United | 1:0 | ||||
| 6. Ronde | 13.09.2008 | Scunthorpe United | - | Carlisle United | 2:1 | ||||
| 7. Ronde | 20.09.2008 | Hereford United | - | Scunthorpe United | 1:2 |  |
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| 8. Ronde | 27.09.2008 | Scunthorpe United | - | Yeovil Town | 2:0 |  |
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| 9. Ronde | 04.10.2008 | Leyton Orient | - | Scunthorpe United | 2:2 | |
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| 10. Ronde | 11.10.2008 | Scunthorpe United | - | Crewe Alexandra | 3:0 | |
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| 12. Ronde | 21.10.2008 | Scunthorpe United | - | Southend United | 1:1 | ||||
| 13. Ronde | 25.10.2008 | Scunthorpe United | - | Millwall FC | 3:2 | ||||
| 14. Ronde | 28.10.2008 | Oldham Athletic | - | Scunthorpe United | 3:0 | |
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| 15. Ronde | 01.11.2008 | Scunthorpe United | - | Swindon Town | 3:3 | ||||
| 16. Ronde | 14.11.2008 | Bristol Rovers | - | Scunthorpe United | 1:2 | |
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| 17. Ronde | 22.11.2008 | Scunthorpe United | - | Leicester City | 1:2 | ||||
| 18. Ronde | 25.11.2008 | Tranmere Rovers | - | Scunthorpe United | 2:0 | ||||
| 20. Ronde | 13.12.2008 | Scunthorpe United | - | Northampton Town | 4:4 |
Engeland