| 26. Round | 17/01/2015 | Oxford United | - | Southend United | 2:3 | ||||
| 27. Round | 24/01/2015 | Portsmouth FC | - | Southend United | 1:2 | ||||
| 28. Round | 31/01/2015 | Southend United | - | York City | 1:0 | ||||
| 29. Round | 07/02/2015 | Shrewsbury Town | - | Southend United | 1:1 | ||||
| 30. Round | 10/02/2015 | Southend United | - | Cheltenham Town | 2:0 | ||||
| 31. Round | 14/02/2015 | Southend United | - | Accrington Stanley | 1:2 | ||||
| 32. Round | 21/02/2015 | Stevenage FC | - | Southend United | 4:2 | ||||
| 34. Round | 03/03/2015 | AFC Wimbledon | - | Southend United | 0:0 | ||||
| 36. Round | 14/03/2015 | Dagenham & Redbridge | - | Southend United | 1:3 | ||||
| 37. Round | 18/03/2015 | Burton Albion | - | Southend United | 2:1 | ||||
| 40. Round | 03/04/2015 | Southend United | - | Mansfield Town | 2:0 | ||||
| 41. Round | 06/04/2015 | Hartlepool United | - | Southend United | 0:1 | ||||
| 42. Round | 11/04/2015 | Southend United | - | Tranmere Rovers | 1:0 | ||||
| 43. Round | 14/04/2015 | Southend United | - | Newport County | 2:0 | ||||
| 44. Round | 18/04/2015 | Exeter City | - | Southend United | 0:1 | ||||
| 39. Round | 21/04/2015 | Bury FC | - | Southend United | 0:1 | ||||
| 45. Round | 25/04/2015 | Southend United | - | Luton Town | 1:0 |
Wales