| 1 | Sat 4 Aug 2018 | 6 2-3 v Doncaster RoversSouthend United 2-3 Doncaster Rovers | Sky Bet League One |
| 2 | Sat 11 Aug 2018 | 61-1 v Plymouth ArgylePlymouth Argyle 1-1 Southend United | Sky Bet League One |
| 3 | Sat 18 Aug 2018 | 62-0 v Bradford CitySouthend United 2-0 Bradford City | Sky Bet League One |
| 4 | Tue 21 Aug 2018 | 60-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League One |
| 5 | Sat 25 Aug 2018 | 61-0 v Bristol RoversBristol Rovers 0-1 Southend United | Sky Bet League One |
| 6 | Sat 1 Sep 2018 | 61-2 v Charlton AthleticSouthend United 1-2 Charlton Athletic | Sky Bet League One |
| 7 | Sat 8 Sep 2018 | 62-3 v Peterborough UnitedSouthend United 2-3 Peterborough United | Sky Bet League One |
| 8 | Sat 22 Sep 2018 | 61-0 v Fleetwood TownSouthend United 1-0 Fleetwood Town | Sky Bet League One |
| 9 | Sat 29 Sep 2018 | 63-2 v Wycombe WanderersWycombe Wanderers 2-3 Southend United | Sky Bet League One |
| 10 | Tue 2 Oct 2018 | 62-1 v Burton AlbionBurton Albion 1-2 Southend United | Sky Bet League One |
| 11 | Sat 6 Oct 2018 | 60-0 v Oxford UnitedSouthend United 0-0 Oxford United | Sky Bet League One |
| 12 | Sat 13 Oct 2018 | 62-0 v GillinghamGillingham 0-2 Southend United | Sky Bet League One |
| 13 | Sat 20 Oct 2018 | 61-2 v Coventry CitySouthend United 1-2 Coventry City | Sky Bet League One |
| 14 | Tue 23 Oct 2018 | 6 3-0 v WalsallSouthend United 3-0 Walsall | Sky Bet League One |
| 15 | Sat 27 Oct 2018 | 60-3 v SunderlandSunderland 3-0 Southend United | Sky Bet League One |
| 16 | Sat 3 Nov 2018 | 60-1 v BarnsleyBarnsley 1-0 Southend United | Sky Bet League One |
| 17 | Sat 10 Nov 2018 | 61-1 v Crawley TownSouthend United 1-1 Crawley Town | Emirates FA Cup First Round |
| 18 | Sat 17 Nov 2018 | 6 1-2 v BlackpoolSouthend United 1-2 Blackpool | Sky Bet League One |
| 19 | Sat 1 Dec 2018 | 62-4 v BarnsleySouthend United 2-4 Barnsley | Emirates FA Cup Second Round |
| 20 | Wed 5 Dec 2018 | 61-1 v Luton TownLuton Town 1-1 Southend United | Checkatrade Trophy Second Round |
| 21 | Sat 8 Dec 2018 | 60-2 v PortsmouthPortsmouth 2-0 Southend United | Sky Bet League One |
| 22 | Wed 26 Dec 2018 | 61-0 v Oxford UnitedOxford United 0-1 Southend United | Sky Bet League One |
| 23 | Tue 1 Jan 2019 | 62-0 v GillinghamSouthend United 2-0 Gillingham | Sky Bet League One |
| 24 | Sat 12 Jan 2019 | 62-3 v Plymouth ArgyleSouthend United 2-3 Plymouth Argyle | Sky Bet League One |
| 25 | Sat 19 Jan 2019 | 64-0 v Bradford CityBradford City 0-4 Southend United | Sky Bet League One |
| 26 | Sat 26 Jan 2019 | 60-1 v Luton TownSouthend United 0-1 Luton Town | Sky Bet League One |
| 27 | Sat 2 Feb 2019 | 6 1-2 v Bristol RoversSouthend United 1-2 Bristol Rovers | Sky Bet League One |
| 28 | Sat 9 Feb 2019 | 61-1 v Charlton AthleticCharlton Athletic 1-1 Southend United | Sky Bet League One |
| 29 | Tue 12 Feb 2019 | 60-3 v Doncaster RoversDoncaster Rovers 3-0 Southend United | Sky Bet League One |
| 30 | Sat 16 Feb 2019 | 63-3 v PortsmouthSouthend United 3-3 Portsmouth | Sky Bet League One |
| 31 | Sat 23 Feb 2019 | 61-1 v Accrington StanleyAccrington Stanley 1-1 Southend United | Sky Bet League One |
| 32 | Sat 2 Mar 2019 | 60-3 v BarnsleySouthend United 0-3 Barnsley | Sky Bet League One |
| 33 | Sat 9 Mar 2019 | 62-2 v BlackpoolBlackpool 2-2 Southend United | Sky Bet League One |
| 34 | Tue 12 Mar 2019 | 61-4 v Scunthorpe UnitedScunthorpe United 4-1 Southend United | Sky Bet League One |
| 35 | Sat 16 Mar 2019 | 60-1 v AFC WimbledonSouthend United 0-1 AFC Wimbledon | Sky Bet League One |
| 36 | Fri 19 Apr 2019 | 6 1-1 v WalsallWalsall 1-1 Southend United | Sky Bet League One |
| 37 | Mon 22 Apr 2019 | 63-2 v Burton AlbionSouthend United 3-2 Burton Albion | Sky Bet League One |
| 38 | Sat 27 Apr 2019 | 60-1 v RochdaleRochdale 1-0 Southend United | Sky Bet League One |
| 39 | Sat 4 May 2019 | 62-1 v SunderlandSouthend United 2-1 Sunderland | Sky Bet League One |
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