| 7. Ronde | 20.09.2008 | Carlisle United | - | Leeds United | 0:2 | ||||
| 8. Ronde | 27.09.2008 | Walsall FC | - | Carlisle United | 2:1 |  |
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| 9. Ronde | 04.10.2008 | Carlisle United | - | Tranmere Rovers | 1:2 | ||||
| 10. Ronde | 11.10.2008 | Milton Keynes Dons | - | Carlisle United | 3:1 | ||||
| 11. Ronde | 18.10.2008 | Carlisle United | - | Peterborough United | 3:3 | ||||
| 12. Ronde | 21.10.2008 | Hereford United | - | Carlisle United | 1:0 | ||||
| 14. Ronde | 28.10.2008 | Carlisle United | - | Hartlepool United | 0:1 | ||||
| 15. Ronde | 01.11.2008 | Stockport County | - | Carlisle United | 3:0 |
Engeland