| 2. Round | 29/11/2008 | Peterborough United | - | Tranmere Rovers | 0:0 | ||||
| 2. Round | 09/12/2008 | Tranmere Rovers | - | Peterborough United | 1:2 aet |  |
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| 3. Round | 03/01/2009 | West Bromwich Albion | - | Peterborough United | 1:1 | ||||
| 3. Round | 13/01/2009 | Peterborough United | - | West Bromwich Albion | 0:2 |
England
Jamaica