| 16. Ronde | 14.11.2009 | Yeovil Town | - | Southend United | 1:0 |  |
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| 18. Ronde | 24.11.2009 | Tranmere Rovers | - | Southend United | 2:0 | ||||
| 19. Ronde | 01.12.2009 | Southend United | - | Norwich City | 0:3 | ||||
| 20. Ronde | 05.12.2009 | Charlton Athletic | - | Southend United | 1:0 | ||||
| 21. Ronde | 12.12.2009 | Southend United | - | Hartlepool United | 3:2 | ||||
| 22. Ronde | 19.12.2009 | Exeter City | - | Southend United | 1:0 | ||||
| 23. Ronde | 26.12.2009 | Southend United | - | Colchester United | 1:2 | ||||
| 24. Ronde | 28.12.2009 | Leyton Orient | - | Southend United | 1:2 |
Engeland
Ierland