| 1 | Sat 19 Sep 2020 | 40-2 v Carlisle UnitedCarlisle United 2-0 Southend United | Sky Bet League Two |
| 2 | Tue 24 Nov 2020 | 4 0-1 v Forest Green RoversSouthend United 0-1 Forest Green Rovers | Sky Bet League Two |
| 3 | Sat 28 Nov 2020 | 40-3 v Bolton WanderersBolton Wanderers 3-0 Southend United | Sky Bet League Two |
| 4 | Sat 5 Dec 2020 | 40-0 v StevenageStevenage 0-0 Southend United | Sky Bet League Two |
| 5 | Sat 12 Dec 2020 | 41-0 v Scunthorpe UnitedSouthend United 1-0 Scunthorpe United | Sky Bet League Two |
| 6 | Tue 15 Dec 2020 | 43-1 v Grimsby TownSouthend United 3-1 Grimsby Town | Sky Bet League Two |
| 7 | Sat 19 Dec 2020 | 41-1 v Mansfield TownMansfield Town 1-1 Southend United | Sky Bet League Two |
| 8 | Sat 9 Jan 2021 | 41-0 v BarrowSouthend United 1-0 Barrow | Sky Bet League Two |
| 9 | Sat 16 Jan 2021 | 4 0-0 v Grimsby TownGrimsby Town 0-0 Southend United | Sky Bet League Two |
| 10 | Tue 19 Jan 2021 | 41-2 v Cambridge UnitedSouthend United 1-2 Cambridge United | Sky Bet League Two |
| 11 | Sat 23 Jan 2021 | 40-1 v Mansfield TownSouthend United 0-1 Mansfield Town | Sky Bet League Two |
| 12 | Wed 24 Feb 2021 | 43-1 v Forest Green RoversForest Green Rovers 1-3 Southend United | Sky Bet League Two |
| 13 | Sat 27 Feb 2021 | 4 0-0 v Salford CitySouthend United 0-0 Salford City | Sky Bet League Two |
| 14 | Tue 9 Mar 2021 | 40-2 v Tranmere RoversSouthend United 0-2 Tranmere Rovers | Sky Bet League Two |
| 15 | Sat 13 Mar 2021 | 4 0-0 v StevenageSouthend United 0-0 Stevenage | Sky Bet League Two |
| 16 | Sat 20 Mar 2021 | 41-1 v Scunthorpe UnitedScunthorpe United 1-1 Southend United | Sky Bet League Two |
| 17 | Tue 23 Mar 2021 | 4 0-0 v WalsallSouthend United 0-0 Walsall | Sky Bet League Two |
| 18 | Sat 27 Mar 2021 | 41-0 v Harrogate TownHarrogate Town 0-1 Southend United | Sky Bet League Two |
| 19 | Sat 3 Apr 2021 | 40-2 v Carlisle UnitedSouthend United 0-2 Carlisle United | Sky Bet League Two |
| 20 | Sat 17 Apr 2021 | 40-0 v Exeter CityExeter City 0-0 Southend United | Sky Bet League Two |
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