| 1 | Sat 4 Aug 2018 | 42-3 v Doncaster RoversSouthend United 2-3 Doncaster Rovers | Sky Bet League One |
| 2 | Tue 21 Aug 2018 | 4 0-2 v Luton TownLuton Town 2-0 Southend United | Sky Bet League One |
| 3 | Tue 20 Nov 2018 | 4 6-2 v Crawley TownCrawley Town 2-6 Southend United | Emirates FA Cup First Round Replay |
| 4 | Tue 27 Nov 2018 | 42-0 v Scunthorpe UnitedSouthend United 2-0 Scunthorpe United | Sky Bet League One |
| 5 | Wed 5 Dec 2018 | 41-1 v Luton TownLuton Town 1-1 Southend United | Checkatrade Trophy Second Round |
| 6 | Sat 8 Dec 2018 | 4 0-2 v PortsmouthPortsmouth 2-0 Southend United | Sky Bet League One |
| 7 | Sat 15 Dec 2018 | 43-0 v Accrington StanleySouthend United 3-0 Accrington Stanley | Sky Bet League One |
| 8 | Sat 22 Dec 2018 | 41-2 v RochdaleSouthend United 1-2 Rochdale | Sky Bet League One |
| 9 | Wed 26 Dec 2018 | 4 1-0 v Oxford UnitedOxford United 0-1 Southend United | Sky Bet League One |
| 10 | Tue 8 Jan 2019 | 40-2 v PortsmouthSouthend United 0-2 Portsmouth | Checkatrade Trophy Third Round |
| 11 | Sat 19 Jan 2019 | 44-0 v Bradford CityBradford City 0-4 Southend United | Sky Bet League One |
| 12 | Sat 23 Feb 2019 | 41-1 v Accrington StanleyAccrington Stanley 1-1 Southend United | Sky Bet League One |
| 13 | Sat 9 Mar 2019 | 4 2-2 v BlackpoolBlackpool 2-2 Southend United | Sky Bet League One |
| 14 | Tue 12 Mar 2019 | 41-4 v Scunthorpe UnitedScunthorpe United 4-1 Southend United | Sky Bet League One |
| 15 | Sat 16 Mar 2019 | 40-1 v AFC WimbledonSouthend United 0-1 AFC Wimbledon | Sky Bet League One |
| 16 | Sat 30 Mar 2019 | 4 0-2 v Shrewsbury TownSouthend United 0-2 Shrewsbury Town | Sky Bet League One |
| 17 | Sat 6 Apr 2019 | 4 2-2 v Fleetwood TownFleetwood Town 2-2 Southend United | Sky Bet League One |
| 18 | Fri 19 Apr 2019 | 41-1 v WalsallWalsall 1-1 Southend United | Sky Bet League One |
| 19 | Sat 27 Apr 2019 | 40-1 v RochdaleRochdale 1-0 Southend United | Sky Bet League One |
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