| 1. Runde | 08.11.2008 | AFC Telford United | - | Southend United | 2:2 | ||||
| 1. Runde | 18.11.2008 | Southend United | - | AFC Telford United | 2:0 | ||||
| 2. Runde | 29.11.2008 | Southend United | - | Luton Town | 3:1 | ||||
| 3. Runde | 03.01.2009 | Chelsea FC | - | Southend United | 1:1 | ||||
| 3. Runde | 14.01.2009 | Southend United | - | Chelsea FC | 1:4 |  |
England