1. Round | 03/08/2019 | Coventry City | - | Southend United | 1:0 | ||||
6. Round | 31/08/2019 | Southend United | - | Rochdale AFC | 0:3 | ||||
9. Round | 17/09/2019 | Shrewsbury Town | - | Southend United | 4:3 | ||||
10. Round | 21/09/2019 | Milton Keynes Dons | - | Southend United | 0:1 | ||||
17. Round | 02/11/2019 | Sunderland AFC | - | Southend United | 1:0 |