| 1 | Tue 21 Aug 2018 | 20-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League One |
| 2 | Sat 25 Aug 2018 | 21-0 v Bristol RoversBristol Rovers 0-1 Southend United | Sky Bet League One |
| 3 | Sat 1 Sep 2018 | 21-2 v Charlton AthleticSouthend United 1-2 Charlton Athletic | Sky Bet League One |
| 4 | Tue 4 Sep 2018 | 23-1 v Cambridge UnitedSouthend United 3-1 Cambridge United | Checkatrade Trophy Southern Group B |
| 5 | Sat 8 Sep 2018 | 22-3 v Peterborough UnitedSouthend United 2-3 Peterborough United | Sky Bet League One |
| 6 | Tue 9 Oct 2018 | 20-2 v Colchester UnitedColchester United 2-0 Southend United | Checkatrade Trophy Southern Group B |
| 7 | Sat 13 Oct 2018 | 22-0 v GillinghamGillingham 0-2 Southend United | Sky Bet League One |
| 8 | Sat 20 Oct 2018 | 21-2 v Coventry CitySouthend United 1-2 Coventry City | Sky Bet League One |
| 9 | Tue 27 Nov 2018 | 22-0 v Scunthorpe UnitedSouthend United 2-0 Scunthorpe United | Sky Bet League One |
| 10 | Sat 1 Dec 2018 | 22-4 v BarnsleySouthend United 2-4 Barnsley | Emirates FA Cup Second Round |
| 11 | Wed 5 Dec 2018 | 21-1 v Luton TownLuton Town 1-1 Southend United | Checkatrade Trophy Second Round |
| 12 | Sat 8 Dec 2018 | 20-2 v PortsmouthPortsmouth 2-0 Southend United | Sky Bet League One |
| 13 | Sat 15 Dec 2018 | 23-0 v Accrington StanleySouthend United 3-0 Accrington Stanley | Sky Bet League One |
| 14 | Sat 22 Dec 2018 | 21-2 v RochdaleSouthend United 1-2 Rochdale | Sky Bet League One |
| 15 | Wed 26 Dec 2018 | 2 1-0 v Oxford UnitedOxford United 0-1 Southend United | Sky Bet League One |
| 16 | Sat 29 Dec 2018 | 20-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 17 | Tue 1 Jan 2019 | 2 2-0 v GillinghamSouthend United 2-0 Gillingham | Sky Bet League One |
| 18 | Tue 8 Jan 2019 | 20-2 v PortsmouthSouthend United 0-2 Portsmouth | Checkatrade Trophy Third Round |
| 19 | Sat 12 Jan 2019 | 22-3 v Plymouth ArgyleSouthend United 2-3 Plymouth Argyle | Sky Bet League One |
| 20 | Sat 19 Jan 2019 | 24-0 v Bradford CityBradford City 0-4 Southend United | Sky Bet League One |
| 21 | Sat 26 Jan 2019 | 20-1 v Luton TownSouthend United 0-1 Luton Town | Sky Bet League One |
| 22 | Sat 2 Feb 2019 | 21-2 v Bristol RoversSouthend United 1-2 Bristol Rovers | Sky Bet League One |
| 23 | Sat 9 Feb 2019 | 21-1 v Charlton AthleticCharlton Athletic 1-1 Southend United | Sky Bet League One |
| 24 | Tue 12 Feb 2019 | 20-3 v Doncaster RoversDoncaster Rovers 3-0 Southend United | Sky Bet League One |
| 25 | Sat 16 Feb 2019 | 23-3 v PortsmouthSouthend United 3-3 Portsmouth | Sky Bet League One |
| 26 | Sat 23 Feb 2019 | 21-1 v Accrington StanleyAccrington Stanley 1-1 Southend United | Sky Bet League One |
| 27 | Sat 2 Mar 2019 | 20-3 v BarnsleySouthend United 0-3 Barnsley | Sky Bet League One |
| 28 | Sat 9 Mar 2019 | 22-2 v BlackpoolBlackpool 2-2 Southend United | Sky Bet League One |
| 29 | Sat 23 Mar 2019 | 20-2 v Peterborough UnitedPeterborough United 2-0 Southend United | Sky Bet League One |
| 30 | Sat 6 Apr 2019 | 22-2 v Fleetwood TownFleetwood Town 2-2 Southend United | Sky Bet League One |
| 31 | Sat 13 Apr 2019 | 20-2 v Wycombe WanderersSouthend United 0-2 Wycombe Wanderers | Sky Bet League One |
| 32 | Fri 19 Apr 2019 | 21-1 v WalsallWalsall 1-1 Southend United | Sky Bet League One |
| 33 | Mon 22 Apr 2019 | 23-2 v Burton AlbionSouthend United 3-2 Burton Albion | Sky Bet League One |
| 34 | Sat 27 Apr 2019 | 20-1 v RochdaleRochdale 1-0 Southend United | Sky Bet League One |
| 35 | Sat 4 May 2019 | 22-1 v SunderlandSouthend United 2-1 Sunderland | Sky Bet League One |
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