| 1 | Sat 31 Aug 2019 | 150-3 v RochdaleSouthend United 0-3 Rochdale | Sky Bet League One |
| 2 | Tue 3 Sep 2019 | 150-2 v Leyton OrientLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 3 | Sat 14 Sep 2019 | 15 3-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
| 4 | Tue 17 Sep 2019 | 153-4 v Shrewsbury TownShrewsbury Town 4-3 Southend United | Sky Bet League One |
| 5 | Sat 21 Sep 2019 | 151-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Southend United | Sky Bet League One |
| 6 | Sat 28 Sep 2019 | 150-1 v Accrington StanleySouthend United 0-1 Accrington Stanley | Sky Bet League One |
| 7 | Sat 5 Oct 2019 | 15 1-3 v GillinghamGillingham 3-1 Southend United | Sky Bet League One |
| 8 | Sat 12 Oct 2019 | 15 1-4 v AFC WimbledonSouthend United 1-4 AFC Wimbledon | Sky Bet League One |
| 9 | Sat 26 Oct 2019 | 151-3 v Ipswich TownSouthend United 1-3 Ipswich Town | Sky Bet League One |
| 10 | Sun 10 Nov 2019 | 150-1 v Dover AthleticDover Athletic 1-0 Southend United | Emirates FA Cup First Round |
| 11 | Wed 13 Nov 2019 | 153-1 v AFC WimbledonSouthend United 3-1 AFC Wimbledon | Leasing.com Trophy Southern Group C |
| 12 | Sat 23 Nov 2019 | 150-4 v Oxford UnitedSouthend United 0-4 Oxford United | Sky Bet League One |
| 13 | Tue 3 Dec 2019 | 151-1 v Burton AlbionBurton Albion 1-1 Southend United | Sky Bet League One |
| 14 | Sat 7 Dec 2019 | 15 2-4 v Bristol RoversBristol Rovers 4-2 Southend United | Sky Bet League One |
| 15 | Sat 14 Dec 2019 | 152-2 v Rotherham UnitedSouthend United 2-2 Rotherham United | Sky Bet League One |
| 16 | Sat 21 Dec 2019 | 152-3 v Bolton WanderersBolton Wanderers 3-2 Southend United | Sky Bet League One |
| 17 | Thu 26 Dec 2019 | 152-2 v Milton Keynes DonsSouthend United 2-2 Milton Keynes Dons | Sky Bet League One |
| 18 | Wed 1 Jan 2020 | 151-1 v AFC WimbledonAFC Wimbledon 1-1 Southend United | Sky Bet League One |
| 19 | Sat 11 Jan 2020 | 150-0 v Tranmere RoversSouthend United 0-0 Tranmere Rovers | Sky Bet League One |
| 20 | Sat 18 Jan 2020 | 152-1 v Accrington StanleyAccrington Stanley 1-2 Southend United | Sky Bet League One |
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