| 1 | Sat 17 Aug 2019 | 0-4 v Lincoln CityLincoln City 4-0 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 | Tue 3 Sep 2019 | 0-2 v Leyton OrientLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 7 | Sat 14 Sep 2019 | 3-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
| 8 | Tue 17 Sep 2019 | 3-4 v Shrewsbury TownShrewsbury Town 4-3 Southend United | Sky Bet League One |
| 9 | Sat 21 Sep 2019 | 1-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Southend United | Sky Bet League One |
| 10 | Sat 28 Sep 2019 | 0-1 v Accrington StanleySouthend United 0-1 Accrington Stanley | Sky Bet League One |
| 11 | Sat 5 Oct 2019 | 1-3 v GillinghamGillingham 3-1 Southend United | Sky Bet League One |
| 12 | Sat 12 Oct 2019 | 1-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
| 13 | Fri 18 Oct 2019 | 1-1 v Tranmere RoversTranmere Rovers 1-1 Southend United | Sky Bet League One |
| 14 | Tue 22 Oct 2019 | 1-7 v Doncaster RoversSouthend United 1-7 Doncaster Rovers | 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 | Wed 13 Nov 2019 | 3-1 v AFC WimbledonSouthend United 3-1 AFC Wimbledon | Leasing.com Trophy Southern Group C |
| 17 | Sat 23 Nov 2019 | 0-4 v Oxford UnitedSouthend United 0-4 Oxford United | Sky Bet League One |
| 18 | Sat 7 Dec 2019 | 2-4 v Bristol RoversBristol Rovers 4-2 Southend United | Sky Bet League One |
| 19 | Sat 11 Jan 2020 | 0-2 v RochdaleRochdale 2-0 Bolton Wanderers | Sky Bet League One |
| 20 | Tue 14 Jan 2020 | 1-5 v Lincoln CityLincoln City 5-1 Bolton Wanderers | Sky Bet League One |
| 21 | Sat 1 Feb 2020 | 2-0 v Tranmere RoversBolton Wanderers 2-0 Tranmere Rovers | Sky Bet League One |
| 22 | Sat 8 Feb 2020 | 1-2 v Coventry CityCoventry City 2-1 Bolton Wanderers | Sky Bet League One |
| 23 | Tue 11 Feb 2020 | 1-2 v Doncaster RoversDoncaster Rovers 2-1 Bolton Wanderers | Sky Bet League One |
| 24 | Sat 15 Feb 2020 | 0-2 v Wycombe WanderersBolton Wanderers 0-2 Wycombe Wanderers | Sky Bet League One |
| 25 | Sat 22 Feb 2020 | 0-1 v Milton Keynes DonsMilton Keynes Dons 1-0 Bolton Wanderers | Sky Bet League One |
| 26 | Tue 25 Feb 2020 | 1-2 v BlackpoolBlackpool 2-1 Bolton Wanderers | Sky Bet League One |
| 27 | Sat 7 Mar 2020 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Bolton Wanderers | Sky Bet League One |
| 28 | Tue 10 Mar 2020 | 2-2 v Burton AlbionBurton Albion 2-2 Bolton Wanderers | Sky Bet League One |
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