1 | Sat 3 Aug 2019 | 0-1 v Coventry CityCoventry City 1-0 Southend United | Sky Bet League One |
2 | Tue 20 Aug 2019 | 0-2 v Peterborough UnitedSouthend United 0-2 Peterborough United | Sky Bet League One |
3 | Sat 24 Aug 2019 | 3-4 v Wycombe WanderersWycombe Wanderers 4-3 Southend United | Sky Bet League One |
4 | Tue 27 Aug 2019 | 1-4 v Milton Keynes DonsSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
5 | Sat 31 Aug 2019 | 0-3 v RochdaleSouthend United 0-3 Rochdale | Sky Bet League One |
6 | Sat 14 Sep 2019 | 3-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
7 | Tue 17 Sep 2019 | 3-4 v Shrewsbury TownShrewsbury Town 4-3 Southend United | Sky Bet League One |
8 | Sat 21 Sep 2019 | 1-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Southend United | Sky Bet League One |
9 | Sat 28 Sep 2019 | 0-1 v Accrington StanleySouthend United 0-1 Accrington Stanley | Sky Bet League One |
10 | Sat 12 Oct 2019 | 1-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
11 | Sat 2 Nov 2019 | 0-1 v SunderlandSunderland 1-0 Southend United | Sky Bet League One |
12 | Sun 10 Nov 2019 | 0-1 v Dover AthleticDover Athletic 1-0 Southend United | Emirates FA Cup First Round |
13 | Sat 23 Nov 2019 | 0-4 v Oxford UnitedSouthend United 0-4 Oxford United | Sky Bet League One |
14 | Tue 3 Dec 2019 | 1-1 v Burton AlbionBurton Albion 1-1 Southend United | Sky Bet League One |
15 | Sat 7 Dec 2019 | 2-4 v Bristol RoversBristol Rovers 4-2 Southend United | Sky Bet League One |
16 | Sat 14 Dec 2019 | 2-2 v Rotherham UnitedSouthend United 2-2 Rotherham United | Sky Bet League One |
17 | Sat 21 Dec 2019 | 2-3 v Bolton WanderersBolton Wanderers 3-2 Southend United | Sky Bet League One |
18 | Thu 26 Dec 2019 | 2-2 v Milton Keynes DonsSouthend United 2-2 Milton Keynes Dons | Sky Bet League One |
19 | Sat 18 Jan 2020 | 2-1 v Accrington StanleyAccrington Stanley 1-2 Southend United | Sky Bet League One |
20 | Sat 8 Feb 2020 | 1-2 v BlackpoolBlackpool 2-1 Southend United | Sky Bet League One |
21 | Sat 15 Feb 2020 | 0-2 v Coventry CitySouthend United 0-2 Coventry City | Sky Bet League One |
22 | Sat 29 Feb 2020 | 1-2 v Oxford UnitedOxford United 2-1 Southend United | Sky Bet League One |