| 1 | Sat 5 Sep 2020 | 52-1 v Forest Green RoversForest Green Rovers 1-2 Leyton Orient | Carabao Cup First Round South |
| 2 | Sat 19 Sep 2020 | 52-2 v Mansfield TownLeyton Orient 2-2 Mansfield Town | Sky Bet League Two |
| 3 | Tue 6 Oct 2020 | 52-0 v AFC WimbledonLeyton Orient 2-0 AFC Wimbledon | Papa John’s Trophy Group 10 |
| 4 | Sat 10 Oct 2020 | 5 1-1 v BarrowBarrow 1-1 Leyton Orient | Sky Bet League Two |
| 5 | Sat 17 Oct 2020 | 52-3 v Grimsby TownLeyton Orient 2-3 Grimsby Town | Sky Bet League Two |
| 6 | Tue 20 Oct 2020 | 51-0 v Tranmere RoversTranmere Rovers 0-1 Leyton Orient | Sky Bet League Two |
| 7 | Sat 24 Oct 2020 | 52-0 v StevenageStevenage 0-2 Leyton Orient | Sky Bet League Two |
| 8 | Tue 27 Oct 2020 | 51-1 v Exeter CityLeyton Orient 1-1 Exeter City | Sky Bet League Two |
| 9 | Sat 31 Oct 2020 | 54-0 v Bolton WanderersLeyton Orient 4-0 Bolton Wanderers | Sky Bet League Two |
| 10 | Tue 3 Nov 2020 | 51-2 v Forest Green RoversForest Green Rovers 2-1 Leyton Orient | Sky Bet League Two |
| 11 | Sat 14 Nov 2020 | 51-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 12 | Sat 21 Nov 2020 | 53-0 v Harrogate TownLeyton Orient 3-0 Harrogate Town | Sky Bet League Two |
| 13 | Tue 24 Nov 2020 | 51-0 v Bradford CityLeyton Orient 1-0 Bradford City | Sky Bet League Two |
| 14 | Sat 28 Nov 2020 | 5 3-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League Two |
| 15 | Sat 5 Dec 2020 | 50-2 v Scunthorpe UnitedScunthorpe United 2-0 Leyton Orient | Sky Bet League Two |
| 16 | Tue 8 Dec 2020 | 51-2 v Bristol RoversLeyton Orient 1-2 Bristol Rovers | Papa John’s Trophy Second Round |
| 17 | Sat 12 Dec 2020 | 52-1 v Newport CountyLeyton Orient 2-1 Newport County | Sky Bet League Two |
| 18 | Tue 15 Dec 2020 | 51-2 v MorecambeMorecambe 2-1 Leyton Orient | Sky Bet League Two |
| 19 | Sat 19 Dec 2020 | 5 1-2 v Crawley TownLeyton Orient 1-2 Crawley Town | Sky Bet League Two |
| 20 | Sat 26 Dec 2020 | 5 1-2 v Cambridge UnitedCambridge United 2-1 Leyton Orient | Sky Bet League Two |
| 21 | Tue 29 Dec 2020 | 52-0 v Southend UnitedLeyton Orient 2-0 Southend United | Sky Bet League Two |
| 22 | Sat 2 Jan 2021 | 51-0 v Salford CityLeyton Orient 1-0 Salford City | Sky Bet League Two |
| 23 | Sat 16 Jan 2021 | 52-0 v MorecambeLeyton Orient 2-0 Morecambe | Sky Bet League Two |
| 24 | Sat 23 Jan 2021 | 5 0-1 v Forest Green RoversLeyton Orient 0-1 Forest Green Rovers | Sky Bet League Two |
| 25 | Sat 6 Feb 2021 | 50-0 v Colchester UnitedLeyton Orient 0-0 Colchester United | Sky Bet League Two |
| 26 | Sat 20 Feb 2021 | 51-1 v Port ValeLeyton Orient 1-1 Port Vale | Sky Bet League Two |
| 27 | Tue 23 Feb 2021 | 50-1 v Bradford CityBradford City 1-0 Leyton Orient | Sky Bet League Two |
| 28 | Sat 27 Feb 2021 | 51-3 v Tranmere RoversLeyton Orient 1-3 Tranmere Rovers | Sky Bet League Two |
| 29 | Tue 2 Mar 2021 | 51-0 v Grimsby TownGrimsby Town 0-1 Leyton Orient | Sky Bet League Two |
| 30 | Sat 6 Mar 2021 | 50-4 v Exeter CityExeter City 4-0 Leyton Orient | Sky Bet League Two |
| 31 | Tue 9 Mar 2021 | 50-0 v StevenageLeyton Orient 0-0 Stevenage | Sky Bet League Two |
| 32 | Sat 13 Mar 2021 | 51-1 v Scunthorpe UnitedLeyton Orient 1-1 Scunthorpe United | Sky Bet League Two |
| 33 | Sat 20 Mar 2021 | 51-0 v Newport CountyNewport County 0-1 Leyton Orient | Sky Bet League Two |
| 34 | Tue 23 Mar 2021 | 51-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League Two |
| 35 | Sat 27 Mar 2021 | 52-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Sky Bet League Two |
| 36 | Sat 10 Apr 2021 | 50-1 v Cheltenham TownCheltenham Town 1-0 Leyton Orient | Sky Bet League Two |
| 37 | Tue 13 Apr 2021 | 52-2 v Harrogate TownHarrogate Town 2-2 Leyton Orient | Sky Bet League Two |
| 38 | Sat 17 Apr 2021 | 52-0 v BarrowLeyton Orient 2-0 Barrow | Sky Bet League Two |
| 39 | Tue 20 Apr 2021 | 52-4 v Cambridge UnitedLeyton Orient 2-4 Cambridge United | Sky Bet League Two |
| 40 | Sat 24 Apr 2021 | 51-2 v Southend UnitedSouthend United 2-1 Leyton Orient | Sky Bet League Two |
| 41 | Sat 1 May 2021 | 5 2-3 v Carlisle UnitedLeyton Orient 2-3 Carlisle United | Sky Bet League Two |
| 42 | Sat 8 May 2021 | 5 0-3 v Salford CitySalford City 3-0 Leyton Orient | Sky Bet League Two |
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