22. Round | 15/12/2018 | Southend United | - | Accrington Stanley | 3:0 | ||||
23. Round | 22/12/2018 | Southend United | - | Rochdale AFC | 1:2 | ||||
25. Round | 29/12/2018 | Coventry City | - | Southend United | 1:0 | ||||
26. Round | 01/01/2019 | Southend United | - | Gillingham FC | 2:0 | ||||
28. Round | 12/01/2019 | Southend United | - | Plymouth Argyle | 2:3 | ||||
33. Round | 16/02/2019 | Southend United | - | Portsmouth FC | 3:3 | ||||
34. Round | 23/02/2019 | Accrington Stanley | - | Southend United | 1:1 | ||||
39. Round | 23/03/2019 | Peterborough United | - | Southend United | 2:0 |