| 1 | Tue 4 Sep 2018 | 30 3-1 v Cambridge UnitedSouthend United 3-1 Cambridge United | Checkatrade Trophy Southern Group B |
| 2 | Sat 8 Sep 2018 | 302-3 v Peterborough UnitedSouthend United 2-3 Peterborough United | Sky Bet League One |
| 3 | Sat 15 Sep 2018 | 300-2 v Shrewsbury TownShrewsbury Town 2-0 Southend United | Sky Bet League One |
| 4 | Sat 20 Oct 2018 | 301-2 v Coventry CitySouthend United 1-2 Coventry City | Sky Bet League One |
| 5 | Tue 23 Oct 2018 | 303-0 v WalsallSouthend United 3-0 Walsall | Sky Bet League One |
| 6 | Sat 27 Oct 2018 | 30 0-3 v SunderlandSunderland 3-0 Southend United | Sky Bet League One |
| 7 | Sat 3 Nov 2018 | 300-1 v BarnsleyBarnsley 1-0 Southend United | Sky Bet League One |
| 8 | Sat 10 Nov 2018 | 301-1 v Crawley TownSouthend United 1-1 Crawley Town | Emirates FA Cup First Round |
| 9 | Sat 17 Nov 2018 | 301-2 v BlackpoolSouthend United 1-2 Blackpool | Sky Bet League One |
| 10 | Tue 20 Nov 2018 | 30 6-2 v Crawley TownCrawley Town 2-6 Southend United | Emirates FA Cup First Round Replay |
| 11 | Sat 24 Nov 2018 | 301-2 v AFC WimbledonAFC Wimbledon 2-1 Southend United | Sky Bet League One |
| 12 | Tue 27 Nov 2018 | 302-0 v Scunthorpe UnitedSouthend United 2-0 Scunthorpe United | Sky Bet League One |
| 13 | Sat 1 Dec 2018 | 302-4 v BarnsleySouthend United 2-4 Barnsley | Emirates FA Cup Second Round |
| 14 | Sat 8 Dec 2018 | 300-2 v PortsmouthPortsmouth 2-0 Southend United | Sky Bet League One |
| 15 | Sat 29 Dec 2018 | 300-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 16 | Tue 1 Jan 2019 | 302-0 v GillinghamSouthend United 2-0 Gillingham | Sky Bet League One |
| 17 | Tue 8 Jan 2019 | 300-2 v PortsmouthSouthend United 0-2 Portsmouth | Checkatrade Trophy Third Round |
| 18 | Sat 12 Jan 2019 | 302-3 v Plymouth ArgyleSouthend United 2-3 Plymouth Argyle | Sky Bet League One |
| 19 | Sat 2 Mar 2019 | 300-3 v BarnsleySouthend United 0-3 Barnsley | Sky Bet League One |
| 20 | Sat 9 Mar 2019 | 302-2 v BlackpoolBlackpool 2-2 Southend United | Sky Bet League One |
| 21 | Tue 12 Mar 2019 | 301-4 v Scunthorpe UnitedScunthorpe United 4-1 Southend United | Sky Bet League One |
| 22 | Sat 16 Mar 2019 | 300-1 v AFC WimbledonSouthend United 0-1 AFC Wimbledon | Sky Bet League One |
| 23 | Sat 23 Mar 2019 | 300-2 v Peterborough UnitedPeterborough United 2-0 Southend United | Sky Bet League One |
| 24 | Sat 30 Mar 2019 | 300-2 v Shrewsbury TownSouthend United 0-2 Shrewsbury Town | Sky Bet League One |
| 25 | Sat 6 Apr 2019 | 302-2 v Fleetwood TownFleetwood Town 2-2 Southend United | Sky Bet League One |
| 26 | Fri 19 Apr 2019 | 301-1 v WalsallWalsall 1-1 Southend United | Sky Bet League One |
| 27 | Mon 22 Apr 2019 | 303-2 v Burton AlbionSouthend United 3-2 Burton Albion | Sky Bet League One |
| 28 | Sat 27 Apr 2019 | 300-1 v RochdaleRochdale 1-0 Southend United | Sky Bet League One |
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