| 1 | Sat 3 Aug 2019 | 0-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
| 2 | Sat 10 Aug 2019 | 1-3 v BlackpoolSouthend United 1-3 Blackpool | Sky Bet League One |
| 3 | Tue 13 Aug 2019 | 2-1 v StevenageStevenage 1-2 Southend United | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 0-4 v Lincoln CityLincoln City 4-0 Southend United | Sky Bet League One |
| 5 | Tue 20 Aug 2019 | 0-2 v Peterborough UnitedSouthend United 0-2 Peterborough United | Sky Bet League One |
| 6 | Sat 24 Aug 2019 | 3-4 v Wycombe WanderersWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 7 | Tue 27 Aug 2019 | 1-4 v Milton Keynes DonsSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 8 | Tue 3 Sep 2019 | 0-2 v Leyton OrientLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 9 | Sat 5 Oct 2019 | 1-3 v GillinghamGillingham 3-1 Southend United | Sky Bet League One |
| 10 | Sat 12 Oct 2019 | 1-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
| 11 | Fri 18 Oct 2019 | 1-1 v Tranmere RoversTranmere Rovers 1-1 Southend United | Sky Bet League One |
| 12 | Tue 22 Oct 2019 | 1-7 v Doncaster RoversSouthend United 1-7 Doncaster Rovers | Sky Bet League One |
| 13 | Sat 26 Oct 2019 | 1-3 v Ipswich TownSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 14 | Sat 2 Nov 2019 | 0-1 v SunderlandSunderland 1-0 Southend United | Sky Bet League One |
| 15 | Sun 10 Nov 2019 | 0-1 v Dover AthleticDover Athletic 1-0 Southend United | Emirates FA Cup First Round |
| 16 | Sat 22 Feb 2020 | 2-3 v Burton AlbionSouthend United 2-3 Burton Albion | Sky Bet League One |
| 17 | Sat 29 Feb 2020 | 1-2 v Oxford UnitedOxford United 2-1 Southend United | Sky Bet League One |
| 18 | Sat 7 Mar 2020 | 3-1 v Bristol RoversSouthend United 3-1 Bristol Rovers | Sky Bet League One |
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