| 1 | Sat 12 Oct 2019 | 91-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
| 2 | Fri 18 Oct 2019 | 91-1 v Tranmere RoversTranmere Rovers 1-1 Southend United | Sky Bet League One |
| 3 | Tue 22 Oct 2019 | 91-7 v Doncaster RoversSouthend United 1-7 Doncaster Rovers | Sky Bet League One |
| 4 | Sat 26 Oct 2019 | 9 1-3 v Ipswich TownSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 5 | Sat 2 Nov 2019 | 9 0-1 v SunderlandSunderland 1-0 Southend United | Sky Bet League One |
| 6 | Sun 10 Nov 2019 | 90-1 v Dover AthleticDover Athletic 1-0 Southend United | Emirates FA Cup First Round |
| 7 | Sat 23 Nov 2019 | 90-4 v Oxford UnitedSouthend United 0-4 Oxford United | Sky Bet League One |
| 8 | Tue 3 Dec 2019 | 91-1 v Burton AlbionBurton Albion 1-1 Southend United | Sky Bet League One |
| 9 | Sat 7 Dec 2019 | 92-4 v Bristol RoversBristol Rovers 4-2 Southend United | Sky Bet League One |
| 10 | Sat 21 Dec 2019 | 92-3 v Bolton WanderersBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 11 | Thu 26 Dec 2019 | 92-2 v Milton Keynes DonsSouthend United 2-2 Milton Keynes Dons | Sky Bet League One |
| 12 | Wed 1 Jan 2020 | 9 1-1 v AFC WimbledonAFC Wimbledon 1-1 Southend United | Sky Bet League One |
| 13 | Sat 11 Jan 2020 | 90-0 v Tranmere RoversSouthend United 0-0 Tranmere Rovers | Sky Bet League One |
| 14 | Sat 18 Jan 2020 | 92-1 v Accrington StanleyAccrington Stanley 1-2 Southend United | Sky Bet League One |
| 15 | Tue 28 Jan 2020 | 0-2 v PortsmouthLincoln City 0-2 Portsmouth | Sky Bet League One |
| 16 | Sat 1 Feb 2020 | 1-2 v Southend UnitedSouthend United 2-1 Lincoln City | Sky Bet League One |
| 17 | Fri 7 Feb 2020 | 0-1 v Rotherham UnitedLincoln City 0-1 Rotherham United | Sky Bet League One |
| 18 | Sat 15 Feb 2020 | 3-4 v Accrington StanleyAccrington Stanley 4-3 Lincoln City | Sky Bet League One |
| 19 | Sat 22 Feb 2020 | 0-0 v GillinghamLincoln City 0-0 Gillingham | Sky Bet League One |
| 20 | Sat 7 Mar 2020 | 3-2 v Burton AlbionLincoln City 3-2 Burton Albion | Sky Bet League One |
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