| 1 | Sat 5 Sep 2020 | 261-2 v Port ValeScunthorpe United 1-2 Port Vale | Carabao Cup First Round North |
| 2 | Sat 19 Sep 2020 | 260-1 v Crawley TownCrawley Town 1-0 Scunthorpe United | Sky Bet League Two |
| 3 | Sat 26 Sep 2020 | 261-0 v Carlisle UnitedScunthorpe United 1-0 Carlisle United | Sky Bet League Two |
| 4 | Sat 3 Oct 2020 | 260-2 v Tranmere RoversTranmere Rovers 2-0 Scunthorpe United | Sky Bet League Two |
| 5 | Sat 10 Oct 2020 | 261-4 v Forest Green RoversScunthorpe United 1-4 Forest Green Rovers | Sky Bet League Two |
| 6 | Sat 17 Oct 2020 | 260-5 v Cambridge UnitedScunthorpe United 0-5 Cambridge United | Sky Bet League Two |
| 7 | Tue 20 Oct 2020 | 260-1 v Cheltenham TownCheltenham Town 1-0 Scunthorpe United | Sky Bet League Two |
| 8 | Tue 10 Nov 2020 | 261-2 v Mansfield TownScunthorpe United 1-2 Mansfield Town | Papa John’s Trophy Group 9 |
| 9 | Tue 15 Dec 2020 | 262-1 v BarrowScunthorpe United 2-1 Barrow | Sky Bet League Two |
| 10 | Sat 26 Dec 2020 | 262-3 v Mansfield TownScunthorpe United 2-3 Mansfield Town | Sky Bet League Two |
| 11 | Tue 29 Dec 2020 | 262-1 v WalsallWalsall 1-2 Scunthorpe United | Sky Bet League Two |
| 12 | Sat 2 Jan 2021 | 261-3 v StevenageStevenage 3-1 Scunthorpe United | Sky Bet League Two |
| 13 | Tue 12 Jan 2021 | 260-1 v Salford CityScunthorpe United 0-1 Salford City | Sky Bet League Two |
| 14 | Tue 26 Jan 2021 | 6 1-3 v Bradford CitySouthend United 1-3 Bradford City | Sky Bet League Two |
| 15 | Sat 30 Jan 2021 | 61-5 v Port ValePort Vale 5-1 Southend United | Sky Bet League Two |
| 16 | Tue 9 Feb 2021 | 61-0 v Newport CountyNewport County 0-1 Southend United | Sky Bet League Two |
| 17 | Tue 2 Mar 2021 | 60-1 v Cheltenham TownCheltenham Town 1-0 Southend United | Sky Bet League Two |
| 18 | Sat 6 Mar 2021 | 60-0 v Oldham AthleticOldham Athletic 0-0 Southend United | Sky Bet League Two |
| 19 | Tue 9 Mar 2021 | 60-2 v Tranmere RoversSouthend United 0-2 Tranmere Rovers | Sky Bet League Two |
| 20 | Sat 27 Mar 2021 | 61-0 v Harrogate TownHarrogate Town 0-1 Southend United | Sky Bet League Two |
| 21 | Sat 3 Apr 2021 | 60-2 v Carlisle UnitedSouthend United 0-2 Carlisle United | Sky Bet League Two |
| 22 | Tue 6 Apr 2021 | 61-1 v MorecambeMorecambe 1-1 Southend United | Sky Bet League Two |
| 23 | Sat 10 Apr 2021 | 60-0 v Crawley TownSouthend United 0-0 Crawley Town | Sky Bet League Two |
| 24 | Tue 20 Apr 2021 | 6 0-2 v Colchester UnitedColchester United 2-0 Southend United | Sky Bet League Two |
| 25 | Sat 24 Apr 2021 | 6 2-1 v Leyton OrientSouthend United 2-1 Leyton Orient | Sky Bet League Two |
| 26 | Sat 1 May 2021 | 6 2-1 v BarrowBarrow 1-2 Southend United | Sky Bet League Two |
| 27 | Sat 8 May 2021 | 61-1 v Newport CountySouthend United 1-1 Newport County | Sky Bet League Two |
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