| 1 | 29/9/2018 | 163-2 v Wycombe WanderersWycombe Wanderers 2-3 Southend United | Sky Bet League One |
| 2 | 2/10/2018 | 16 2-1 v Burton AlbionBurton Albion 1-2 Southend United | Sky Bet League One |
| 3 | 6/10/2018 | 160-0 v Oxford UnitedSouthend United 0-0 Oxford United | Sky Bet League One |
| 4 | 13/10/2018 | 162-0 v GillinghamGillingham 0-2 Southend United | Sky Bet League One |
| 5 | 20/10/2018 | 161-2 v Coventry CitySouthend United 1-2 Coventry City | Sky Bet League One |
| 6 | 23/10/2018 | 163-0 v WalsallSouthend United 3-0 Walsall | Sky Bet League One |
| 7 | 27/10/2018 | 16 0-3 v SunderlandSunderland 3-0 Southend United | Sky Bet League One |
| 8 | 3/11/2018 | 160-1 v BarnsleyBarnsley 1-0 Southend United | Sky Bet League One |
| 9 | 10/11/2018 | 161-1 v Crawley TownSouthend United 1-1 Crawley Town | Emirates FA Cup First Round |
| 10 | 17/11/2018 | 161-2 v BlackpoolSouthend United 1-2 Blackpool | Sky Bet League One |
| 11 | 24/11/2018 | 161-2 v AFC WimbledonAFC Wimbledon 2-1 Southend United | Sky Bet League One |
| 12 | 1/12/2018 | 162-4 v BarnsleySouthend United 2-4 Barnsley | Emirates FA Cup Second Round |
| 13 | 5/12/2018 | 16 1-1 v Luton TownLuton Town 1-1 Southend United | Checkatrade Trophy Second Round |
| 14 | 8/12/2018 | 160-2 v PortsmouthPortsmouth 2-0 Southend United | Sky Bet League One |
| 15 | 15/12/2018 | 163-0 v Accrington StanleySouthend United 3-0 Accrington Stanley | Sky Bet League One |
| 16 | 26/12/2018 | 161-0 v Oxford UnitedOxford United 0-1 Southend United | Sky Bet League One |
| 17 | 29/12/2018 | 160-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 18 | 1/1/2019 | 162-0 v GillinghamSouthend United 2-0 Gillingham | Sky Bet League One |
| 19 | 8/1/2019 | 160-2 v PortsmouthSouthend United 0-2 Portsmouth | Checkatrade Trophy Third Round |
| 20 | 12/1/2019 | 162-3 v Plymouth ArgyleSouthend United 2-3 Plymouth Argyle | Sky Bet League One |
| 21 | 19/1/2019 | 164-0 v Bradford CityBradford City 0-4 Southend United | Sky Bet League One |
| 22 | 26/1/2019 | 16 0-1 v Luton TownSouthend United 0-1 Luton Town | Sky Bet League One |
| 23 | 2/2/2019 | 16 1-2 v Bristol RoversSouthend United 1-2 Bristol Rovers | Sky Bet League One |
| 24 | 9/2/2019 | 16 1-1 v Charlton AthleticCharlton Athletic 1-1 Southend United | Sky Bet League One |
| 25 | 2/3/2019 | 160-3 v BarnsleySouthend United 0-3 Barnsley | Sky Bet League One |
| 26 | 16/3/2019 | 160-1 v AFC WimbledonSouthend United 0-1 AFC Wimbledon | Sky Bet League One |
| 27 | 23/3/2019 | 160-2 v Peterborough UnitedPeterborough United 2-0 Southend United | Sky Bet League One |
| 28 | 30/3/2019 | 160-2 v Shrewsbury TownSouthend United 0-2 Shrewsbury Town | Sky Bet League One |
| 29 | 19/4/2019 | 161-1 v WalsallWalsall 1-1 Southend United | Sky Bet League One |
| 30 | 22/4/2019 | 163-2 v Burton AlbionSouthend United 3-2 Burton Albion | Sky Bet League One |
| 31 | 4/5/2019 | 162-1 v SunderlandSouthend United 2-1 Sunderland | Sky Bet League One |
