17. Round | 22/11/2008 | Carlisle United | - | Cheltenham Town | 1:0 | ||||
18. Round | 25/11/2008 | Millwall FC | - | Carlisle United | 1:0 | ||||
19. Round | 06/12/2008 | Swindon Town | - | Carlisle United | 1:1 | ||||
20. Round | 13/12/2008 | Carlisle United | - | Leicester City | 1:2 | ||||
21. Round | 20/12/2008 | Northampton Town | - | Carlisle United | 1:0 | ||||
22. Round | 26/12/2008 | Carlisle United | - | Huddersfield Town | 3:0 | ||||
23. Round | 28/12/2008 | Oldham Athletic | - | Carlisle United | 0:0 | ||||
25. Round | 10/01/2009 | Leeds United | - | Carlisle United | 0:2 | ||||
26. Round | 17/01/2009 | Carlisle United | - | Milton Keynes Dons | 3:2 |