| 1 | Sat 4 Aug 2018 | 312-3 v Doncaster RoversSouthend United 2-3 Doncaster Rovers | Sky Bet League One |
| 2 | Sat 11 Aug 2018 | 311-1 v Plymouth ArgylePlymouth Argyle 1-1 Southend United | Sky Bet League One |
| 3 | Tue 14 Aug 2018 | 312-4 v BrentfordSouthend United 2-4 Brentford | Carabao Cup First Round |
| 4 | Sat 18 Aug 2018 | 312-0 v Bradford CitySouthend United 2-0 Bradford City | Sky Bet League One |
| 5 | Tue 21 Aug 2018 | 310-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League One |
| 6 | Sat 25 Aug 2018 | 311-0 v Bristol RoversBristol Rovers 0-1 Southend United | Sky Bet League One |
| 7 | Sat 1 Sep 2018 | 311-2 v Charlton AthleticSouthend United 1-2 Charlton Athletic | Sky Bet League One |
| 8 | Sat 8 Sep 2018 | 312-3 v Peterborough UnitedSouthend United 2-3 Peterborough United | Sky Bet League One |
| 9 | Sat 22 Sep 2018 | 311-0 v Fleetwood TownSouthend United 1-0 Fleetwood Town | Sky Bet League One |
| 10 | Sat 29 Sep 2018 | 313-2 v Wycombe WanderersWycombe Wanderers 2-3 Southend United | Sky Bet League One |
| 11 | Tue 2 Oct 2018 | 312-1 v Burton AlbionBurton Albion 1-2 Southend United | Sky Bet League One |
| 12 | Sat 6 Oct 2018 | 310-0 v Oxford UnitedSouthend United 0-0 Oxford United | Sky Bet League One |
| 13 | Tue 9 Oct 2018 | 310-2 v Colchester UnitedColchester United 2-0 Southend United | Checkatrade Trophy Southern Group B |
| 14 | Sat 13 Oct 2018 | 312-0 v GillinghamGillingham 0-2 Southend United | Sky Bet League One |
| 15 | Sat 20 Oct 2018 | 311-2 v Coventry CitySouthend United 1-2 Coventry City | Sky Bet League One |
| 16 | Sat 3 Nov 2018 | 310-1 v BarnsleyBarnsley 1-0 Southend United | Sky Bet League One |
| 17 | Sat 10 Nov 2018 | 311-1 v Crawley TownSouthend United 1-1 Crawley Town | Emirates FA Cup First Round |
| 18 | Sat 17 Nov 2018 | 311-2 v BlackpoolSouthend United 1-2 Blackpool | Sky Bet League One |
| 19 | Tue 20 Nov 2018 | 316-2 v Crawley TownCrawley Town 2-6 Southend United | Emirates FA Cup First Round Replay |
| 20 | Sat 24 Nov 2018 | 311-2 v AFC WimbledonAFC Wimbledon 2-1 Southend United | Sky Bet League One |
| 21 | Sat 1 Dec 2018 | 312-4 v BarnsleySouthend United 2-4 Barnsley | Emirates FA Cup Second Round |
| 22 | Wed 5 Dec 2018 | 311-1 v Luton TownLuton Town 1-1 Southend United | Checkatrade Trophy Second Round |
| 23 | Sat 8 Dec 2018 | 310-2 v PortsmouthPortsmouth 2-0 Southend United | Sky Bet League One |
| 24 | Sat 15 Dec 2018 | 313-0 v Accrington StanleySouthend United 3-0 Accrington Stanley | Sky Bet League One |
| 25 | Sat 22 Dec 2018 | 311-2 v RochdaleSouthend United 1-2 Rochdale | Sky Bet League One |
| 26 | Wed 26 Dec 2018 | 311-0 v Oxford UnitedOxford United 0-1 Southend United | Sky Bet League One |
| 27 | Sat 29 Dec 2018 | 310-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 28 | Tue 1 Jan 2019 | 31 2-0 v GillinghamSouthend United 2-0 Gillingham | Sky Bet League One |
| 29 | Tue 8 Jan 2019 | 310-2 v PortsmouthSouthend United 0-2 Portsmouth | Checkatrade Trophy Third Round |
| 30 | Sat 19 Jan 2019 | 314-0 v Bradford CityBradford City 0-4 Southend United | Sky Bet League One |
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