| 1 | Tue 14 Aug 2018 | 2-4 v BrentfordSouthend United 2-4 Brentford | Carabao Cup First Round |
| 2 | Tue 21 Aug 2018 | 280-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League One |
| 3 | Sat 1 Sep 2018 | 281-2 v Charlton AthleticSouthend United 1-2 Charlton Athletic | Sky Bet League One |
| 4 | Tue 4 Sep 2018 | 283-1 v Cambridge UnitedSouthend United 3-1 Cambridge United | Checkatrade Trophy Southern Group B |
| 5 | Sat 8 Sep 2018 | 282-3 v Peterborough UnitedSouthend United 2-3 Peterborough United | Sky Bet League One |
| 6 | Sat 22 Sep 2018 | 281-0 v Fleetwood TownSouthend United 1-0 Fleetwood Town | Sky Bet League One |
| 7 | Tue 2 Oct 2018 | 282-1 v Burton AlbionBurton Albion 1-2 Southend United | Sky Bet League One |
| 8 | Sat 6 Oct 2018 | 280-0 v Oxford UnitedSouthend United 0-0 Oxford United | Sky Bet League One |
| 9 | Tue 9 Oct 2018 | 280-2 v Colchester UnitedColchester United 2-0 Southend United | Checkatrade Trophy Southern Group B |
| 10 | Sat 13 Oct 2018 | 282-0 v GillinghamGillingham 0-2 Southend United | Sky Bet League One |
| 11 | Tue 23 Oct 2018 | 283-0 v WalsallSouthend United 3-0 Walsall | Sky Bet League One |
| 12 | Sat 27 Oct 2018 | 280-3 v SunderlandSunderland 3-0 Southend United | Sky Bet League One |
| 13 | Sat 3 Nov 2018 | 280-1 v BarnsleyBarnsley 1-0 Southend United | Sky Bet League One |
| 14 | Sat 17 Nov 2018 | 281-2 v BlackpoolSouthend United 1-2 Blackpool | Sky Bet League One |
| 15 | Tue 20 Nov 2018 | 286-2 v Crawley TownCrawley Town 2-6 Southend United | Emirates FA Cup First Round Replay |
| 16 | Sat 24 Nov 2018 | 281-2 v AFC WimbledonAFC Wimbledon 2-1 Southend United | Sky Bet League One |
| 17 | Tue 27 Nov 2018 | 282-0 v Scunthorpe UnitedSouthend United 2-0 Scunthorpe United | Sky Bet League One |
| 18 | Sat 1 Dec 2018 | 282-4 v BarnsleySouthend United 2-4 Barnsley | Emirates FA Cup Second Round |
| 19 | Wed 5 Dec 2018 | 281-1 v Luton TownLuton Town 1-1 Southend United | Checkatrade Trophy Second Round |
| 20 | Sat 22 Dec 2018 | 281-2 v RochdaleSouthend United 1-2 Rochdale | Sky Bet League One |
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