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