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