| 1 | Tue 4 Sep 2018 | 133-1 v Cambridge UnitedSouthend United 3-1 Cambridge United | Checkatrade Trophy Southern Group B |
| 2 | Tue 9 Oct 2018 | 130-2 v Colchester UnitedColchester United 2-0 Southend United | Checkatrade Trophy Southern Group B |
| 3 | Sat 22 Dec 2018 | 131-2 v RochdaleSouthend United 1-2 Rochdale | Sky Bet League One |
| 4 | Wed 26 Dec 2018 | 131-0 v Oxford UnitedOxford United 0-1 Southend United | Sky Bet League One |
| 5 | Sat 29 Dec 2018 | 130-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 6 | Tue 1 Jan 2019 | 132-0 v GillinghamSouthend United 2-0 Gillingham | Sky Bet League One |
| 7 | Sat 12 Jan 2019 | 132-3 v Plymouth ArgyleSouthend United 2-3 Plymouth Argyle | Sky Bet League One |
| 8 | Sat 19 Jan 2019 | 134-0 v Bradford CityBradford City 0-4 Southend United | Sky Bet League One |
| 9 | Sat 26 Jan 2019 | 130-1 v Luton TownSouthend United 0-1 Luton Town | Sky Bet League One |
| 10 | Sat 2 Feb 2019 | 131-2 v Bristol RoversSouthend United 1-2 Bristol Rovers | Sky Bet League One |
| 11 | Sat 9 Feb 2019 | 131-1 v Charlton AthleticCharlton Athletic 1-1 Southend United | Sky Bet League One |
| 12 | Tue 12 Feb 2019 | 130-3 v Doncaster RoversDoncaster Rovers 3-0 Southend United | Sky Bet League One |
| 13 | Sat 16 Feb 2019 | 133-3 v PortsmouthSouthend United 3-3 Portsmouth | Sky Bet League One |
| 14 | Sat 23 Feb 2019 | 131-1 v Accrington StanleyAccrington Stanley 1-1 Southend United | Sky Bet League One |
| 15 | Sat 2 Mar 2019 | 130-3 v BarnsleySouthend United 0-3 Barnsley | Sky Bet League One |
| 16 | Sat 9 Mar 2019 | 132-2 v BlackpoolBlackpool 2-2 Southend United | Sky Bet League One |
| 17 | Tue 12 Mar 2019 | 131-4 v Scunthorpe UnitedScunthorpe United 4-1 Southend United | Sky Bet League One |
| 18 | Sat 30 Mar 2019 | 130-2 v Shrewsbury TownSouthend United 0-2 Shrewsbury Town | Sky Bet League One |
| 19 | Sat 6 Apr 2019 | 132-2 v Fleetwood TownFleetwood Town 2-2 Southend United | Sky Bet League One |
| 20 | Sat 13 Apr 2019 | 130-2 v Wycombe WanderersSouthend United 0-2 Wycombe Wanderers | Sky Bet League One |
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