1. Round | 03/08/2019 | Coventry City | - | Southend United | 1:0 | ||||
2. Round | 10/08/2019 | Southend United | - | Blackpool FC | 1:3 | ||||
4. Round | 20/08/2019 | Southend United | - | Peterborough United | 0:2 | ||||
5. Round | 24/08/2019 | Wycombe Wanderers | - | Southend United | 4:3 | ||||
6. Round | 31/08/2019 | Southend United | - | Rochdale AFC | 0:3 | ||||
8. Round | 14/09/2019 | Southend United | - | Fleetwood Town | 3:3 | ||||
9. Round | 17/09/2019 | Shrewsbury Town | - | Southend United | 4:3 | ||||
10. Round | 21/09/2019 | Milton Keynes Dons | - | Southend United | 0:1 | ||||
11. Round | 28/09/2019 | Southend United | - | Accrington Stanley | 0:1 | ||||
12. Round | 05/10/2019 | Gillingham FC | - | Southend United | 3:1 | ||||
13. Round | 12/10/2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
15. Round | 22/10/2019 | Southend United | - | Doncaster Rovers | 1:7 | ||||
17. Round | 02/11/2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
7. Round | 05/11/2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
21. Round | 14/12/2019 | Southend United | - | Rotherham United | 2:2 | ||||
22. Round | 21/12/2019 | Bolton Wanderers | - | Southend United | 3:2 |