2. Round | 11/08/2018 | Plymouth Argyle | - | Southend United | 1:1 | ||||
3. Round | 18/08/2018 | Southend United | - | Bradford City | 2:0 | ||||
5. Round | 25/08/2018 | Bristol Rovers | - | Southend United | 0:1 | ||||
9. Round | 22/09/2018 | Southend United | - | Fleetwood Town | 1:0 | ||||
11. Round | 02/10/2018 | Burton Albion | - | Southend United | 1:2 | ||||
32. Round | 09/02/2019 | Charlton Athletic | - | Southend United | 1:1 | ||||
27. Round | 12/02/2019 | Doncaster Rovers | - | Southend United | 3:0 | ||||
33. Round | 16/02/2019 | Southend United | - | Portsmouth FC | 3:3 | ||||
34. Round | 23/02/2019 | Accrington Stanley | - | Southend United | 1:1 | ||||
35. Round | 02/03/2019 | Southend United | - | Barnsley FC | 0:3 |