| 1 | Sat 4 Aug 2018 | 32-3 v Doncaster RoversSouthend United 2-3 Doncaster Rovers | Sky Bet League One |
| 2 | Sat 11 Aug 2018 | 31-1 v Plymouth ArgylePlymouth Argyle 1-1 Southend United | Sky Bet League One |
| 3 | Tue 14 Aug 2018 | 32-4 v BrentfordSouthend United 2-4 Brentford | Carabao Cup First Round |
| 4 | Sat 18 Aug 2018 | 32-0 v Bradford CitySouthend United 2-0 Bradford City | Sky Bet League One |
| 5 | Tue 21 Aug 2018 | 30-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League One |
| 6 | Sat 25 Aug 2018 | 3 1-0 v Bristol RoversBristol Rovers 0-1 Southend United | Sky Bet League One |
| 7 | Sat 1 Sep 2018 | 31-2 v Charlton AthleticSouthend United 1-2 Charlton Athletic | Sky Bet League One |
| 8 | Sat 8 Sep 2018 | 32-3 v Peterborough UnitedSouthend United 2-3 Peterborough United | Sky Bet League One |
| 9 | Sat 15 Sep 2018 | 30-2 v Shrewsbury TownShrewsbury Town 2-0 Southend United | Sky Bet League One |
| 10 | Sat 22 Sep 2018 | 31-0 v Fleetwood TownSouthend United 1-0 Fleetwood Town | Sky Bet League One |
| 11 | Sat 29 Sep 2018 | 33-2 v Wycombe WanderersWycombe Wanderers 2-3 Southend United | Sky Bet League One |
| 12 | Tue 2 Oct 2018 | 32-1 v Burton AlbionBurton Albion 1-2 Southend United | Sky Bet League One |
| 13 | Sat 6 Oct 2018 | 30-0 v Oxford UnitedSouthend United 0-0 Oxford United | Sky Bet League One |
| 14 | Sat 13 Oct 2018 | 32-0 v GillinghamGillingham 0-2 Southend United | Sky Bet League One |
| 15 | Sat 20 Oct 2018 | 3 1-2 v Coventry CitySouthend United 1-2 Coventry City | Sky Bet League One |
| 16 | Tue 23 Oct 2018 | 33-0 v WalsallSouthend United 3-0 Walsall | Sky Bet League One |
| 17 | Sat 27 Oct 2018 | 30-3 v SunderlandSunderland 3-0 Southend United | Sky Bet League One |
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