| 1 | Sat 5 Sep 2020 | 5 0-1 v GillinghamGillingham 1-0 Southend United | Carabao Cup First Round South |
| 2 | Sat 19 Sep 2020 | 50-2 v Carlisle UnitedCarlisle United 2-0 Southend United | Sky Bet League Two |
| 3 | Sat 26 Sep 2020 | 51-2 v MorecambeSouthend United 1-2 Morecambe | Sky Bet League Two |
| 4 | Sat 3 Oct 2020 | 51-1 v Crawley TownCrawley Town 1-1 Southend United | Sky Bet League Two |
| 5 | Tue 6 Oct 2020 | 50-3 v PortsmouthSouthend United 0-3 Portsmouth | Papa John’s Trophy Group 8 |
| 6 | Sat 10 Oct 2020 | 52-2 v Exeter CitySouthend United 2-2 Exeter City | Sky Bet League Two |
| 7 | Sat 17 Oct 2020 | 50-2 v Cheltenham TownSouthend United 0-2 Cheltenham Town | Sky Bet League Two |
| 8 | Tue 20 Oct 2020 | 50-3 v Salford CitySalford City 3-0 Southend United | Sky Bet League Two |
| 9 | Tue 27 Oct 2020 | 51-2 v Oldham AthleticSouthend United 1-2 Oldham Athletic | Sky Bet League Two |
| 10 | Sat 31 Oct 2020 | 50-2 v Port ValeSouthend United 0-2 Port Vale | Sky Bet League Two |
| 11 | Tue 3 Nov 2020 | 50-3 v Bradford CityBradford City 3-0 Southend United | Sky Bet League Two |
| 12 | Tue 10 Nov 2020 | 5 1-6 v Colchester UnitedColchester United 6-1 Southend United | Papa John’s Trophy Group 9 |
| 13 | Sat 14 Nov 2020 | 51-0 v WalsallWalsall 0-1 Southend United | Sky Bet League Two |
| 14 | Tue 24 Nov 2020 | 50-1 v Forest Green RoversSouthend United 0-1 Forest Green Rovers | Sky Bet League Two |
| 15 | Sat 28 Nov 2020 | 50-3 v Bolton WanderersBolton Wanderers 3-0 Southend United | Sky Bet League Two |
| 16 | Sat 5 Dec 2020 | 50-0 v StevenageStevenage 0-0 Southend United | Sky Bet League Two |
| 17 | Sat 12 Dec 2020 | 51-0 v Scunthorpe UnitedSouthend United 1-0 Scunthorpe United | Sky Bet League Two |
| 18 | Tue 15 Dec 2020 | 53-1 v Grimsby TownSouthend United 3-1 Grimsby Town | Sky Bet League Two |
| 19 | Sat 19 Dec 2020 | 51-1 v Mansfield TownMansfield Town 1-1 Southend United | Sky Bet League Two |
| 20 | Sat 26 Dec 2020 | 5 2-0 v Colchester UnitedSouthend United 2-0 Colchester United | Sky Bet League Two |
| 21 | Tue 29 Dec 2020 | 50-2 v Leyton OrientLeyton Orient 2-0 Southend United | Sky Bet League Two |
| 22 | Sat 9 Jan 2021 | 51-0 v BarrowSouthend United 1-0 Barrow | Sky Bet League Two |
| 23 | Sat 16 Jan 2021 | 50-0 v Grimsby TownGrimsby Town 0-0 Southend United | Sky Bet League Two |
| 24 | Tue 19 Jan 2021 | 51-2 v Cambridge UnitedSouthend United 1-2 Cambridge United | Sky Bet League Two |
| 25 | Sat 23 Jan 2021 | 50-1 v Mansfield TownSouthend United 0-1 Mansfield Town | Sky Bet League Two |
| 26 | Tue 26 Jan 2021 | 51-3 v Bradford CitySouthend United 1-3 Bradford City | Sky Bet League Two |
| 27 | Sat 30 Jan 2021 | 5 1-5 v Port ValePort Vale 5-1 Southend United | Sky Bet League Two |
| 28 | Tue 9 Feb 2021 | 51-0 v Newport CountyNewport County 0-1 Southend United | Sky Bet League Two |
| 29 | Sat 13 Feb 2021 | 50-0 v Cambridge UnitedCambridge United 0-0 Southend United | Sky Bet League Two |
| 30 | Sat 20 Feb 2021 | 50-1 v Bolton WanderersSouthend United 0-1 Bolton Wanderers | Sky Bet League Two |
| 31 | Wed 24 Feb 2021 | 5 3-1 v Forest Green RoversForest Green Rovers 1-3 Southend United | Sky Bet League Two |
| 32 | Sat 27 Feb 2021 | 50-0 v Salford CitySouthend United 0-0 Salford City | Sky Bet League Two |
| 33 | Tue 2 Mar 2021 | 50-1 v Cheltenham TownCheltenham Town 1-0 Southend United | Sky Bet League Two |
| 34 | Sat 6 Mar 2021 | 50-0 v Oldham AthleticOldham Athletic 0-0 Southend United | Sky Bet League Two |
| 35 | Sat 13 Mar 2021 | 50-0 v StevenageSouthend United 0-0 Stevenage | Sky Bet League Two |
| 36 | Sat 20 Mar 2021 | 51-1 v Scunthorpe UnitedScunthorpe United 1-1 Southend United | Sky Bet League Two |
| 37 | Tue 23 Mar 2021 | 50-0 v WalsallSouthend United 0-0 Walsall | Sky Bet League Two |
| 38 | Sat 27 Mar 2021 | 5 1-0 v Harrogate TownHarrogate Town 0-1 Southend United | Sky Bet League Two |
| 39 | Sat 3 Apr 2021 | 50-2 v Carlisle UnitedSouthend United 0-2 Carlisle United | Sky Bet League Two |
| 40 | Tue 6 Apr 2021 | 51-1 v MorecambeMorecambe 1-1 Southend United | Sky Bet League Two |
| 41 | Sat 10 Apr 2021 | 50-0 v Crawley TownSouthend United 0-0 Crawley Town | Sky Bet League Two |
| 42 | Sat 17 Apr 2021 | 50-0 v Exeter CityExeter City 0-0 Southend United | Sky Bet League Two |
| 43 | Tue 20 Apr 2021 | 50-2 v Colchester UnitedColchester United 2-0 Southend United | Sky Bet League Two |
| 44 | Sat 24 Apr 2021 | 52-1 v Leyton OrientSouthend United 2-1 Leyton Orient | Sky Bet League Two |
| 45 | Sat 1 May 2021 | 52-1 v BarrowBarrow 1-2 Southend United | Sky Bet League Two |
| 46 | Sat 8 May 2021 | 5 1-1 v Newport CountySouthend United 1-1 Newport County | Sky Bet League Two |
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