1. Round | 04/08/2018 | Southend United | - | Doncaster Rovers | 2:3 | ||||
2. Round | 11/08/2018 | Plymouth Argyle | - | Southend United | 1:1 | ||||
3. Round | 18/08/2018 | Southend United | - | Bradford City | 2:0 | ||||
4. Round | 21/08/2018 | Luton Town | - | Southend United | 2:0 | ||||
5. Round | 25/08/2018 | Bristol Rovers | - | Southend United | 0:1 | ||||
6. Round | 01/09/2018 | Southend United | - | Charlton Athletic | 1:2 | ||||
7. Round | 08/09/2018 | Southend United | - | Peterborough United | 2:3 | ||||
8. Round | 15/09/2018 | Shrewsbury Town | - | Southend United | 2:0 | ||||
9. Round | 22/09/2018 | Southend United | - | Fleetwood Town | 1:0 | ||||
10. Round | 29/09/2018 | Wycombe Wanderers | - | Southend United | 2:3 | ||||
11. Round | 02/10/2018 | Burton Albion | - | Southend United | 1:2 | ||||
12. Round | 06/10/2018 | Southend United | - | Oxford United | 0:0 | ||||
14. Round | 20/10/2018 | Southend United | - | Coventry City | 1:2 | ||||
15. Round | 23/10/2018 | Southend United | - | Walsall FC | 3:0 |