| 1. Round | 08/11/2008 | AFC Telford United | - | Southend United | 2:2 | ||||
| 1. Round | 18/11/2008 | Southend United | - | AFC Telford United | 2:0 | ||||
| 2. Round | 29/11/2008 | Southend United | - | Luton Town | 3:1 | ||||
| 3. Round | 03/01/2009 | Chelsea FC | - | Southend United | 1:1 |  |
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| 3. Round | 14/01/2009 | Southend United | - | Chelsea FC | 1:4 |
England