| 8. Round | 25/09/2010 | Hereford United | - | Southend United | 1:3 | ||||
| 9. Round | 28/09/2010 | Gillingham FC | - | Southend United | 0:0 | ||||
| 10. Round | 02/10/2010 | Southend United | - | Lincoln City | 1:0 | ||||
| 11. Round | 09/10/2010 | Chesterfield FC | - | Southend United | 2:1 | ||||
| 12. Round | 16/10/2010 | Southend United | - | Crewe Alexandra | 0:2 | ||||
| 13. Round | 23/10/2010 | Bury FC | - | Southend United | 1:0 |
Wales