1. Round | 04/08/2018 | Southend United | - | Doncaster Rovers | 2:3 | ||||
13. Round | 13/10/2018 | Gillingham FC | - | Southend United | 0:2 | ||||
15. Round | 23/10/2018 | Southend United | - | Walsall FC | 3:0 | ||||
34. Round | 23/02/2019 | Accrington Stanley | - | Southend United | 1:1 | ||||
36. Round | 09/03/2019 | Blackpool FC | - | Southend United | 2:2 | ||||
37. Round | 12/03/2019 | Scunthorpe United | - | Southend United | 4:1 | ||||
38. Round | 16/03/2019 | Southend United | - | AFC Wimbledon | 0:1 | ||||
41. Round | 06/04/2019 | Fleetwood Town | - | Southend United | 2:2 | ||||
42. Round | 13/04/2019 | Southend United | - | Wycombe Wanderers | 0:2 |