| 1 | 5/9/2020 | 10-1 v GillinghamGillingham 1-0 Southend United | Carabao Cup First Round South |
| 2 | 19/9/2020 | 10-2 v Carlisle UnitedCarlisle United 2-0 Southend United | Sky Bet League Two |
| 3 | 26/9/2020 | 11-2 v MorecambeSouthend United 1-2 Morecambe | Sky Bet League Two |
| 4 | 3/10/2020 | 11-1 v Crawley TownCrawley Town 1-1 Southend United | Sky Bet League Two |
| 5 | 6/10/2020 | 10-3 v PortsmouthSouthend United 0-3 Portsmouth | Checkatrade Trophy Group 8 |
| 6 | 10/10/2020 | 12-2 v Exeter CitySouthend United 2-2 Exeter City | Sky Bet League Two |
| 7 | 17/10/2020 | 10-2 v Cheltenham TownSouthend United 0-2 Cheltenham Town | Sky Bet League Two |
| 8 | 20/10/2020 | 10-3 v Salford CitySalford City 3-0 Southend United | Sky Bet League Two |
| 9 | 24/10/2020 | 10-2 v Tranmere RoversTranmere Rovers 2-0 Southend United | Sky Bet League Two |
| 10 | 27/10/2020 | 11-2 v Oldham AthleticSouthend United 1-2 Oldham Athletic | Sky Bet League Two |
| 11 | 31/10/2020 | 10-2 v Port ValeSouthend United 0-2 Port Vale | Sky Bet League Two |
| 12 | 3/11/2020 | 10-3 v Bradford CityBradford City 3-0 Southend United | Sky Bet League Two |
| 13 | 14/11/2020 | 11-0 v WalsallWalsall 0-1 Southend United | Sky Bet League Two |
| 14 | 24/11/2020 | 10-1 v Forest Green RoversSouthend United 0-1 Forest Green Rovers | Sky Bet League Two |
| 15 | 28/11/2020 | 10-3 v Bolton WanderersBolton Wanderers 3-0 Southend United | Sky Bet League Two |
| 16 | 5/12/2020 | 10-0 v StevenageStevenage 0-0 Southend United | Sky Bet League Two |
| 17 | 12/12/2020 | 11-0 v Scunthorpe UnitedSouthend United 1-0 Scunthorpe United | Sky Bet League Two |
| 18 | 15/12/2020 | 13-1 v Grimsby TownSouthend United 3-1 Grimsby Town | Sky Bet League Two |
| 19 | 19/12/2020 | 11-1 v Mansfield TownMansfield Town 1-1 Southend United | Sky Bet League Two |
| 20 | 26/12/2020 | 12-0 v Colchester UnitedSouthend United 2-0 Colchester United | Sky Bet League Two |
| 21 | 29/12/2020 | 10-2 v Leyton OrientLeyton Orient 2-0 Southend United | Sky Bet League Two |
| 22 | 9/1/2021 | 1 1-0 v BarrowSouthend United 1-0 Barrow | Sky Bet League Two |
| 23 | 16/1/2021 | 10-0 v Grimsby TownGrimsby Town 0-0 Southend United | Sky Bet League Two |
| 24 | 19/1/2021 | 1 1-2 v Cambridge UnitedSouthend United 1-2 Cambridge United | Sky Bet League Two |
| 25 | 23/1/2021 | 10-1 v Mansfield TownSouthend United 0-1 Mansfield Town | Sky Bet League Two |
| 26 | 26/1/2021 | 11-3 v Bradford CitySouthend United 1-3 Bradford City | Sky Bet League Two |
| 27 | 30/1/2021 | 11-5 v Port ValePort Vale 5-1 Southend United | Sky Bet League Two |
| 28 | 9/2/2021 | 11-0 v Newport CountyNewport County 0-1 Southend United | Sky Bet League Two |
| 29 | 13/2/2021 | 10-0 v Cambridge UnitedCambridge United 0-0 Southend United | Sky Bet League Two |
| 30 | 20/2/2021 | 10-1 v Bolton WanderersSouthend United 0-1 Bolton Wanderers | Sky Bet League Two |
| 31 | 24/2/2021 | 13-1 v Forest Green RoversForest Green Rovers 1-3 Southend United | Sky Bet League Two |
| 32 | 20/3/2021 | 11-1 v Scunthorpe UnitedScunthorpe United 1-1 Southend United | Sky Bet League Two |
| 33 | 23/3/2021 | 10-0 v WalsallSouthend United 0-0 Walsall | Sky Bet League Two |
| 34 | 27/3/2021 | 11-0 v Harrogate TownHarrogate Town 0-1 Southend United | Sky Bet League Two |
| 35 | 3/4/2021 | 10-2 v Carlisle UnitedSouthend United 0-2 Carlisle United | Sky Bet League Two |
| 36 | 6/4/2021 | 11-1 v MorecambeMorecambe 1-1 Southend United | Sky Bet League Two |
| 37 | 10/4/2021 | 10-0 v Crawley TownSouthend United 0-0 Crawley Town | Sky Bet League Two |
| 38 | 17/4/2021 | 10-0 v Exeter CityExeter City 0-0 Southend United | Sky Bet League Two |
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