| 1 | Sat 5 Sep 2020 | 220-1 v GillinghamGillingham 1-0 Southend United | Carabao Cup First Round South |
| 2 | Sat 19 Sep 2020 | 220-2 v Carlisle UnitedCarlisle United 2-0 Southend United | Sky Bet League Two |
| 3 | Sat 26 Sep 2020 | 22 1-2 v MorecambeSouthend United 1-2 Morecambe | Sky Bet League Two |
| 4 | Sat 3 Oct 2020 | 221-1 v Crawley TownCrawley Town 1-1 Southend United | Sky Bet League Two |
| 5 | Tue 6 Oct 2020 | 22 0-3 v PortsmouthSouthend United 0-3 Portsmouth | Papa John’s Trophy Group 8 |
| 6 | Tue 20 Oct 2020 | 22 0-3 v Salford CitySalford City 3-0 Southend United | Sky Bet League Two |
| 7 | Tue 10 Nov 2020 | 221-6 v Colchester UnitedColchester United 6-1 Southend United | Papa John’s Trophy Group 9 |
| 8 | Sat 28 Nov 2020 | 220-3 v Bolton WanderersBolton Wanderers 3-0 Southend United | Sky Bet League Two |
| 9 | Sat 5 Dec 2020 | 22 0-0 v StevenageStevenage 0-0 Southend United | Sky Bet League Two |
| 10 | Sat 19 Dec 2020 | 22 1-1 v Mansfield TownMansfield Town 1-1 Southend United | Sky Bet League Two |
| 11 | Tue 29 Dec 2020 | 220-2 v Leyton OrientLeyton Orient 2-0 Southend United | Sky Bet League Two |
| 12 | Sat 9 Jan 2021 | 221-0 v BarrowSouthend United 1-0 Barrow | Sky Bet League Two |
| 13 | Tue 26 Jan 2021 | 221-3 v Bradford CitySouthend United 1-3 Bradford City | Sky Bet League Two |
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