| 1. Round | 09/08/2008 | Scunthorpe United | - | Leeds United | 1:2 |  |
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| 2. Round | 16/08/2008 | Leeds United | - | Oldham Athletic | 0:2 | ||||
| 3. Round | 23/08/2008 | Yeovil Town | - | Leeds United | 1:1 | ||||
| 4. Round | 30/08/2008 | Leeds United | - | Bristol Rovers | 2:2 | ||||
| 11. Round | 18/10/2008 | Millwall FC | - | Leeds United | 3:1 | ||||
| 19. Round | 06/12/2008 | Tranmere Rovers | - | Leeds United | 2:1 | |
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| 20. Round | 13/12/2008 | Leeds United | - | Colchester United | 1:2 | ||||
| 21. Round | 20/12/2008 | Milton Keynes Dons | - | Leeds United | 3:1 |
England