| 1 | 3/8/2019 | 260-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 2 | 10/8/2019 | 261-3 v BlackpoolSouthend United 1-3 Blackpool | Sky Bet League One |
| 3 | 13/8/2019 | 262-1 v StevenageStevenage 1-2 Southend United | Carabao Cup First Round |
| 4 | 20/8/2019 | 260-2 v Peterborough UnitedSouthend United 0-2 Peterborough United | Sky Bet League One |
| 5 | 24/8/2019 | 26 3-4 v Wycombe WanderersWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 6 | 27/8/2019 | 261-4 v Milton Keynes DonsSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 7 | 31/8/2019 | 260-3 v RochdaleSouthend United 0-3 Rochdale | Sky Bet League One |
| 8 | 3/9/2019 | 260-2 v Leyton OrientLeyton Orient 2-0 Southend United | Checkatrade Trophy Southern Group C |
| 9 | 14/9/2019 | 263-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
| 10 | 17/9/2019 | 263-4 v Shrewsbury TownShrewsbury Town 4-3 Southend United | Sky Bet League One |
| 11 | 21/9/2019 | 26 1-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Southend United | Sky Bet League One |
| 12 | 28/9/2019 | 260-1 v Accrington StanleySouthend United 0-1 Accrington Stanley | Sky Bet League One |
| 13 | 5/10/2019 | 26 1-3 v GillinghamGillingham 3-1 Southend United | Sky Bet League One |
| 14 | 12/10/2019 | 261-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
| 15 | 18/10/2019 | 261-1 v Tranmere RoversTranmere Rovers 1-1 Southend United | Sky Bet League One |
| 16 | 22/10/2019 | 26 1-7 v Doncaster RoversSouthend United 1-7 Doncaster Rovers | Sky Bet League One |
| 17 | 2/11/2019 | 260-1 v SunderlandSunderland 1-0 Southend United | Sky Bet League One |
| 18 | 10/11/2019 | 260-1 v Dover AthleticDover Athletic 1-0 Southend United | Emirates FA Cup First Round |
