| 17. Ronde | 22.11.2008 | Carlisle United | - | Cheltenham Town | 1:0 | ||||
| 18. Ronde | 25.11.2008 | Millwall FC | - | Carlisle United | 1:0 | ||||
| 19. Ronde | 06.12.2008 | Swindon Town | - | Carlisle United | 1:1 | ||||
| 20. Ronde | 13.12.2008 | Carlisle United | - | Leicester City | 1:2 |  |
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| 21. Ronde | 20.12.2008 | Northampton Town | - | Carlisle United | 1:0 | ||||
| 22. Ronde | 26.12.2008 | Carlisle United | - | Huddersfield Town | 3:0 | ||||
| 23. Ronde | 28.12.2008 | Oldham Athletic | - | Carlisle United | 0:0 | ||||
| 25. Ronde | 10.01.2009 | Leeds United | - | Carlisle United | 0:2 | ||||
| 26. Ronde | 17.01.2009 | Carlisle United | - | Milton Keynes Dons | 3:2 |
Nederland
