| 1 | 3/8/2019 | 0-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 2 | 10/8/2019 | 1-3 v BlackpoolSouthend United 1-3 Blackpool | Sky Bet League One |
| 3 | 13/8/2019 | 2-1 v StevenageStevenage 1-2 Southend United | Carabao Cup First Round |
| 4 | 17/8/2019 | 0-4 v Lincoln CityLincoln City 4-0 Southend United | Sky Bet League One |
| 5 | 20/8/2019 | 0-2 v Peterborough UnitedSouthend United 0-2 Peterborough United | Sky Bet League One |
| 6 | 24/8/2019 | 3-4 v Wycombe WanderersWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 7 | 27/8/2019 | 1-4 v Milton Keynes DonsSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 8 | 31/8/2019 | 0-3 v RochdaleSouthend United 0-3 Rochdale | Sky Bet League One |
| 9 | 3/9/2019 | 0-2 v Leyton OrientLeyton Orient 2-0 Southend United | Checkatrade Trophy Southern Group C |
| 10 | 14/9/2019 | 3-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
| 11 | 21/9/2019 | 1-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Southend United | Sky Bet League One |
