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