| 1 | Tue 4 Sep 2018 | 3-1 v Cambridge UnitedSouthend United 3-1 Cambridge United | Checkatrade Trophy Southern Group B |
| 2 | Tue 9 Oct 2018 | 0-2 v Colchester UnitedColchester United 2-0 Southend United | Checkatrade Trophy Southern Group B |
| 3 | Sat 15 Dec 2018 | 363-0 v Accrington StanleySouthend United 3-0 Accrington Stanley | Sky Bet League One |
| 4 | Sat 22 Dec 2018 | 361-2 v RochdaleSouthend United 1-2 Rochdale | Sky Bet League One |
| 5 | Sat 29 Dec 2018 | 360-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 6 | Tue 1 Jan 2019 | 362-0 v GillinghamSouthend United 2-0 Gillingham | Sky Bet League One |
| 7 | Tue 8 Jan 2019 | 360-2 v PortsmouthSouthend United 0-2 Portsmouth | Checkatrade Trophy Third Round |
| 8 | Sat 12 Jan 2019 | 362-3 v Plymouth ArgyleSouthend United 2-3 Plymouth Argyle | Sky Bet League One |
| 9 | Sat 16 Feb 2019 | 363-3 v PortsmouthSouthend United 3-3 Portsmouth | Sky Bet League One |
| 10 | Sat 23 Feb 2019 | 361-1 v Accrington StanleyAccrington Stanley 1-1 Southend United | Sky Bet League One |
| 11 | Sat 23 Mar 2019 | 360-2 v Peterborough UnitedPeterborough United 2-0 Southend United | Sky Bet League One |
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