36. Round | 09/03/2019 | Blackpool FC | - | Southend United | 2:2 | ||||
38. Round | 16/03/2019 | Southend United | - | AFC Wimbledon | 0:1 | ||||
39. Round | 23/03/2019 | Peterborough United | - | Southend United | 2:0 | ||||
40. Round | 30/03/2019 | Southend United | - | Shrewsbury Town | 0:2 | ||||
41. Round | 06/04/2019 | Fleetwood Town | - | Southend United | 2:2 | ||||
42. Round | 13/04/2019 | Southend United | - | Wycombe Wanderers | 0:2 | ||||
43. Round | 19/04/2019 | Walsall FC | - | Southend United | 1:1 | ||||
44. Round | 22/04/2019 | Southend United | - | Burton Albion | 3:2 | ||||
45. Round | 27/04/2019 | Rochdale AFC | - | Southend United | 1:0 | ||||
46. Round | 04/05/2019 | Southend United | - | Sunderland AFC | 2:1 |