| 1. Round | 09/08/2008 | Swindon Town | - | Tranmere Rovers | 3:1 | ||||
| 2. Round | 16/08/2008 | Tranmere Rovers | - | Hartlepool United | 1:0 | ||||
| 3. Round | 23/08/2008 | Leicester City | - | Tranmere Rovers | 3:1 |  |
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| 8. Round | 26/09/2008 | Tranmere Rovers | - | Colchester United | 3:4 | ||||
| 9. Round | 04/10/2008 | Carlisle United | - | Tranmere Rovers | 1:2 | ||||
| 11. Round | 18/10/2008 | Leyton Orient | - | Tranmere Rovers | 0:1 |
Ireland