| 1 | Sat 12 Oct 2019 | 8 1-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
| 2 | Fri 18 Oct 2019 | 8 1-1 v Tranmere RoversTranmere Rovers 1-1 Southend United | Sky Bet League One |
| 3 | Tue 22 Oct 2019 | 81-7 v Doncaster RoversSouthend United 1-7 Doncaster Rovers | Sky Bet League One |
| 4 | Sat 26 Oct 2019 | 81-3 v Ipswich TownSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 5 | Sat 2 Nov 2019 | 80-1 v SunderlandSunderland 1-0 Southend United | Sky Bet League One |
| 6 | Sun 10 Nov 2019 | 8 0-1 v Dover AthleticDover Athletic 1-0 Southend United | Emirates FA Cup First Round |
| 7 | Wed 13 Nov 2019 | 83-1 v AFC WimbledonSouthend United 3-1 AFC Wimbledon | Leasing.com Trophy Southern Group C |
| 8 | Sat 23 Nov 2019 | 80-4 v Oxford UnitedSouthend United 0-4 Oxford United | Sky Bet League One |
| 9 | Tue 3 Dec 2019 | 8 1-1 v Burton AlbionBurton Albion 1-1 Southend United | Sky Bet League One |
| 10 | Sat 7 Dec 2019 | 82-4 v Bristol RoversBristol Rovers 4-2 Southend United | Sky Bet League One |
| 11 | Sat 14 Dec 2019 | 82-2 v Rotherham UnitedSouthend United 2-2 Rotherham United | Sky Bet League One |
| 12 | Sat 21 Dec 2019 | 82-3 v Bolton WanderersBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 13 | Thu 26 Dec 2019 | 8 2-2 v Milton Keynes DonsSouthend United 2-2 Milton Keynes Dons | Sky Bet League One |
| 14 | Wed 1 Jan 2020 | 81-1 v AFC WimbledonAFC Wimbledon 1-1 Southend United | Sky Bet League One |
| 15 | Sat 11 Jan 2020 | 80-0 v Tranmere RoversSouthend United 0-0 Tranmere Rovers | Sky Bet League One |
| 16 | Sat 18 Jan 2020 | 82-1 v Accrington StanleyAccrington Stanley 1-2 Southend United | Sky Bet League One |
| 17 | Sat 8 Feb 2020 | 81-2 v BlackpoolBlackpool 2-1 Southend United | Sky Bet League One |
| 18 | Tue 11 Feb 2020 | 80-4 v Peterborough UnitedPeterborough United 4-0 Southend United | Sky Bet League One |
| 19 | Sat 15 Feb 2020 | 80-2 v Coventry CitySouthend United 0-2 Coventry City | Sky Bet League One |
| 20 | Sat 22 Feb 2020 | 82-3 v Burton AlbionSouthend United 2-3 Burton Albion | Sky Bet League One |
| 21 | Sat 29 Feb 2020 | 81-2 v Oxford UnitedOxford United 2-1 Southend United | Sky Bet League One |
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