| 1 | Sat 20 Feb 2021 | 300-1 v Bolton WanderersSouthend United 0-1 Bolton Wanderers | Sky Bet League Two |
| 2 | Wed 24 Feb 2021 | 303-1 v Forest Green RoversForest Green Rovers 1-3 Southend United | Sky Bet League Two |
| 3 | Tue 2 Mar 2021 | 300-1 v Cheltenham TownCheltenham Town 1-0 Southend United | Sky Bet League Two |
| 4 | Tue 9 Mar 2021 | 300-2 v Tranmere RoversSouthend United 0-2 Tranmere Rovers | Sky Bet League Two |
| 5 | Sat 13 Mar 2021 | 300-0 v StevenageSouthend United 0-0 Stevenage | Sky Bet League Two |
| 6 | Sat 27 Mar 2021 | 301-0 v Harrogate TownHarrogate Town 0-1 Southend United | Sky Bet League Two |
| 7 | Tue 6 Apr 2021 | 301-1 v MorecambeMorecambe 1-1 Southend United | Sky Bet League Two |
| 8 | Sat 10 Apr 2021 | 300-0 v Crawley TownSouthend United 0-0 Crawley Town | Sky Bet League Two |
| 9 | Sat 17 Apr 2021 | 300-0 v Exeter CityExeter City 0-0 Southend United | Sky Bet League Two |
| 10 | Tue 20 Apr 2021 | 300-2 v Colchester UnitedColchester United 2-0 Southend United | Sky Bet League Two |
| 11 | Sat 24 Apr 2021 | 302-1 v Leyton OrientSouthend United 2-1 Leyton Orient | Sky Bet League Two |
| 12 | Sat 1 May 2021 | 302-1 v BarrowBarrow 1-2 Southend United | Sky Bet League Two |
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