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 | ||||
6. Round | 31/08/2019 | Southend United | - | Rochdale AFC | 0:3 | ||||
10. Round | 21/09/2019 | Milton Keynes Dons | - | Southend United | 0:1 | ||||
22. Round | 21/12/2019 | Bolton Wanderers | - | Southend United | 3:2 | ||||
23. Round | 26/12/2019 | Southend United | - | Milton Keynes Dons | 2:2 | ||||
27. Round | 11/01/2020 | Southend United | - | Tranmere Rovers | 0:0 | ||||
28. Round | 18/01/2020 | Accrington Stanley | - | Southend United | 1:2 | ||||
30. Round | 28/01/2020 | Doncaster Rovers | - | Southend United | 3:1 | ||||
31. Round | 01/02/2020 | Southend United | - | Lincoln City | 2:1 |