14. Round | 24/10/2009 | Carlisle United | - | Southend United | 2:1 | ||||
25. Round | 26/01/2010 | Millwall FC | - | Southend United | 2:0 | ||||
26. Round | 23/03/2010 | Southend United | - | Walsall FC | 3:0 | ||||
40. Round | 05/04/2010 | Gillingham FC | - | Southend United | 3:0 | ||||
41. Round | 10/04/2010 | Leeds United | - | Southend United | 2:0 | ||||
45. Round | 01/05/2010 | Southend United | - | Stockport County | 2:1 | ||||
46. Round | 08/05/2010 | Southampton FC | - | Southend United | 3:1 |