| 1 | 11/8/2018 | 48 1-1 v Plymouth ArgylePlymouth Argyle 1-1 Southend United | Sky Bet League One |
| 2 | 14/8/2018 | 482-4 v BrentfordSouthend United 2-4 Brentford | Carabao Cup First Round |
| 3 | 18/8/2018 | 482-0 v Bradford CitySouthend United 2-0 Bradford City | Sky Bet League One |
| 4 | 21/8/2018 | 480-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League One |
| 5 | 25/8/2018 | 481-0 v Bristol RoversBristol Rovers 0-1 Southend United | Sky Bet League One |
| 6 | 1/9/2018 | 48 1-2 v Charlton AthleticSouthend United 1-2 Charlton Athletic | Sky Bet League One |
| 7 | 4/9/2018 | 483-1 v Cambridge UnitedSouthend United 3-1 Cambridge United | Checkatrade Trophy Southern Group B |
| 8 | 8/9/2018 | 482-3 v Peterborough UnitedSouthend United 2-3 Peterborough United | Sky Bet League One |
| 9 | 15/9/2018 | 480-2 v Shrewsbury TownShrewsbury Town 2-0 Southend United | Sky Bet League One |
| 10 | 22/9/2018 | 481-0 v Fleetwood TownSouthend United 1-0 Fleetwood Town | Sky Bet League One |
| 11 | 29/9/2018 | 483-2 v Wycombe WanderersWycombe Wanderers 2-3 Southend United | Sky Bet League One |
| 12 | 2/10/2018 | 482-1 v Burton AlbionBurton Albion 1-2 Southend United | Sky Bet League One |
| 13 | 6/10/2018 | 480-0 v Oxford UnitedSouthend United 0-0 Oxford United | Sky Bet League One |
| 14 | 3/11/2018 | 480-1 v BarnsleyBarnsley 1-0 Southend United | Sky Bet League One |
| 15 | 10/11/2018 | 48 1-1 v Crawley TownSouthend United 1-1 Crawley Town | Emirates FA Cup First Round |
| 16 | 20/11/2018 | 486-2 v Crawley TownCrawley Town 2-6 Southend United | Emirates FA Cup First Round Replay |
| 17 | 24/11/2018 | 481-2 v AFC WimbledonAFC Wimbledon 2-1 Southend United | Sky Bet League One |
| 18 | 27/11/2018 | 482-0 v Scunthorpe UnitedSouthend United 2-0 Scunthorpe United | Sky Bet League One |
| 19 | 1/12/2018 | 482-4 v BarnsleySouthend United 2-4 Barnsley | Emirates FA Cup Second Round |
| 20 | 5/12/2018 | 481-1 v Luton TownLuton Town 1-1 Southend United | Checkatrade Trophy Second Round |
| 21 | 8/12/2018 | 48 0-2 v PortsmouthPortsmouth 2-0 Southend United | Sky Bet League One |
| 22 | 15/12/2018 | 483-0 v Accrington StanleySouthend United 3-0 Accrington Stanley | Sky Bet League One |
| 23 | 22/12/2018 | 481-2 v RochdaleSouthend United 1-2 Rochdale | Sky Bet League One |
| 24 | 26/12/2018 | 481-0 v Oxford UnitedOxford United 0-1 Southend United | Sky Bet League One |
| 25 | 29/12/2018 | 480-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 26 | 8/1/2019 | 480-2 v PortsmouthSouthend United 0-2 Portsmouth | Checkatrade Trophy Third Round |
| 27 | 12/1/2019 | 482-3 v Plymouth ArgyleSouthend United 2-3 Plymouth Argyle | Sky Bet League One |
| 28 | 19/1/2019 | 484-0 v Bradford CityBradford City 0-4 Southend United | Sky Bet League One |
| 29 | 26/1/2019 | 480-1 v Luton TownSouthend United 0-1 Luton Town | Sky Bet League One |
| 30 | 2/2/2019 | 481-2 v Bristol RoversSouthend United 1-2 Bristol Rovers | Sky Bet League One |
| 31 | 9/2/2019 | 481-1 v Charlton AthleticCharlton Athletic 1-1 Southend United | Sky Bet League One |
| 32 | 12/2/2019 | 480-3 v Doncaster RoversDoncaster Rovers 3-0 Southend United | Sky Bet League One |
| 33 | 30/3/2019 | 480-2 v Shrewsbury TownSouthend United 0-2 Shrewsbury Town | Sky Bet League One |
| 34 | 6/4/2019 | 48 2-2 v Fleetwood TownFleetwood Town 2-2 Southend United | Sky Bet League One |
| 35 | 13/4/2019 | 480-2 v Wycombe WanderersSouthend United 0-2 Wycombe Wanderers | Sky Bet League One |
| 36 | 19/4/2019 | 48 1-1 v WalsallWalsall 1-1 Southend United | Sky Bet League One |
| 37 | 22/4/2019 | 483-2 v Burton AlbionSouthend United 3-2 Burton Albion | Sky Bet League One |
| 38 | 27/4/2019 | 480-1 v RochdaleRochdale 1-0 Southend United | Sky Bet League One |
| 39 | 4/5/2019 | 482-1 v SunderlandSouthend United 2-1 Sunderland | Sky Bet League One |
