| 1 | 19/1/2019 | 4-0 v Bradford CityBradford City 0-4 Southend United | Sky Bet League One |
| 2 | 26/1/2019 | 0-1 v Luton TownSouthend United 0-1 Luton Town | Sky Bet League One |
| 3 | 2/2/2019 | 1-2 v Bristol RoversSouthend United 1-2 Bristol Rovers | Sky Bet League One |
| 4 | 9/2/2019 | 1-1 v Charlton AthleticCharlton Athletic 1-1 Southend United | Sky Bet League One |
| 5 | 12/2/2019 | 0-3 v Doncaster RoversDoncaster Rovers 3-0 Southend United | Sky Bet League One |
| 6 | 16/2/2019 | 3-3 v PortsmouthSouthend United 3-3 Portsmouth | Sky Bet League One |
| 7 | 23/2/2019 | 1-1 v Accrington StanleyAccrington Stanley 1-1 Southend United | Sky Bet League One |
| 8 | 2/3/2019 | 0-3 v BarnsleySouthend United 0-3 Barnsley | Sky Bet League One |
| 9 | 9/3/2019 | 2-2 v BlackpoolBlackpool 2-2 Southend United | Sky Bet League One |
| 10 | 12/3/2019 | 1-4 v Scunthorpe UnitedScunthorpe United 4-1 Southend United | Sky Bet League One |
| 11 | 16/3/2019 | 0-1 v AFC WimbledonSouthend United 0-1 AFC Wimbledon | Sky Bet League One |
| 12 | 23/3/2019 | 0-2 v Peterborough UnitedPeterborough United 2-0 Southend United | Sky Bet League One |
| 13 | 30/3/2019 | 0-2 v Shrewsbury TownSouthend United 0-2 Shrewsbury Town | Sky Bet League One |
| 14 | 6/4/2019 | 2-2 v Fleetwood TownFleetwood Town 2-2 Southend United | Sky Bet League One |
| 15 | 13/4/2019 | 0-2 v Wycombe WanderersSouthend United 0-2 Wycombe Wanderers | Sky Bet League One |
| 16 | 19/4/2019 | 1-1 v WalsallWalsall 1-1 Southend United | Sky Bet League One |
| 17 | 22/4/2019 | 3-2 v Burton AlbionSouthend United 3-2 Burton Albion | Sky Bet League One |
| 18 | 4/5/2019 | 2-1 v SunderlandSouthend United 2-1 Sunderland | Sky Bet League One |
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