1. Round | 03/08/2019 | Coventry City | - | Southend United | 1:0 | ||||
2. Round | 10/08/2019 | Southend United | - | Blackpool FC | 1:3 | ||||
3. Round | 17/08/2019 | Lincoln City | - | Southend United | 4:0 | ||||
4. Round | 20/08/2019 | Southend United | - | Peterborough United | 0:2 | ||||
5. Round | 24/08/2019 | Wycombe Wanderers | - | Southend United | 4:3 | ||||
12. Round | 05/10/2019 | Gillingham FC | - | Southend United | 3:1 | ||||
13. Round | 12/10/2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
14. Round | 18/10/2019 | Tranmere Rovers | - | Southend United | 1:1 | ||||
15. Round | 22/10/2019 | Southend United | - | Doncaster Rovers | 1:7 | ||||
16. Round | 26/10/2019 | Southend United | - | Ipswich Town | 1:3 | ||||
17. Round | 02/11/2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
7. Round | 05/11/2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
26. Round | 18/02/2020 | Southend United | - | Gillingham FC | 0:1 | ||||
35. Round | 22/02/2020 | Southend United | - | Burton Albion | 2:3 | ||||
36. Round | 29/02/2020 | Oxford United | - | Southend United | 2:1 | ||||
37. Round | 07/03/2020 | Southend United | - | Bristol Rovers | 3:1 |