| 1 | Tue 15 Sep 2020 | 33-2 v Plymouth ArgyleLeyton Orient 3-2 Plymouth Argyle | Carabao Cup Second Round |
| 2 | Sat 3 Oct 2020 | 30-2 v Cheltenham TownLeyton Orient 0-2 Cheltenham Town | Sky Bet League Two |
| 3 | Tue 6 Oct 2020 | 32-0 v AFC WimbledonLeyton Orient 2-0 AFC Wimbledon | Papa John’s Trophy Group 10 |
| 4 | Sat 10 Oct 2020 | 31-1 v BarrowBarrow 1-1 Leyton Orient | Sky Bet League Two |
| 5 | Tue 13 Oct 2020 | 3 1-2 v WalsallWalsall 2-1 Leyton Orient | Sky Bet League Two |
| 6 | Tue 20 Oct 2020 | 31-0 v Tranmere RoversTranmere Rovers 0-1 Leyton Orient | Sky Bet League Two |
| 7 | Tue 27 Oct 2020 | 3 1-1 v Exeter CityLeyton Orient 1-1 Exeter City | Sky Bet League Two |
| 8 | Sat 31 Oct 2020 | 34-0 v Bolton WanderersLeyton Orient 4-0 Bolton Wanderers | Sky Bet League Two |
| 9 | Tue 3 Nov 2020 | 31-2 v Forest Green RoversForest Green Rovers 2-1 Leyton Orient | Sky Bet League Two |
| 10 | Tue 10 Nov 2020 | 31-3 v Charlton AthleticCharlton Athletic 3-1 Leyton Orient | Papa John’s Trophy Group 10 |
| 11 | Sat 21 Nov 2020 | 3 3-0 v Harrogate TownLeyton Orient 3-0 Harrogate Town | Sky Bet League Two |
| 12 | Tue 24 Nov 2020 | 31-0 v Bradford CityLeyton Orient 1-0 Bradford City | Sky Bet League Two |
| 13 | Sat 28 Nov 2020 | 33-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League Two |
| 14 | Sat 5 Dec 2020 | 3 0-2 v Scunthorpe UnitedScunthorpe United 2-0 Leyton Orient | Sky Bet League Two |
| 15 | Tue 8 Dec 2020 | 31-2 v Bristol RoversLeyton Orient 1-2 Bristol Rovers | Papa John’s Trophy Second Round |
| 16 | Sat 12 Dec 2020 | 3 2-1 v Newport CountyLeyton Orient 2-1 Newport County | Sky Bet League Two |
| 17 | Sat 19 Dec 2020 | 31-2 v Crawley TownLeyton Orient 1-2 Crawley Town | Sky Bet League Two |
| 18 | Sat 26 Dec 2020 | 31-2 v Cambridge UnitedCambridge United 2-1 Leyton Orient | Sky Bet League Two |
| 19 | Sat 30 Jan 2021 | 30-2 v Bolton WanderersBolton Wanderers 2-0 Leyton Orient | Sky Bet League Two |
| 20 | Tue 2 Feb 2021 | 30-0 v Crawley TownCrawley Town 0-0 Leyton Orient | Sky Bet League Two |
| 21 | Tue 2 Mar 2021 | 31-0 v Grimsby TownGrimsby Town 0-1 Leyton Orient | Sky Bet League Two |
| 22 | Sat 6 Mar 2021 | 3 0-4 v Exeter CityExeter City 4-0 Leyton Orient | Sky Bet League Two |
| 23 | Sat 20 Mar 2021 | 31-0 v Newport CountyNewport County 0-1 Leyton Orient | Sky Bet League Two |
| 24 | Tue 23 Mar 2021 | 31-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League Two |
| 25 | Sat 27 Mar 2021 | 32-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Sky Bet League Two |
| 26 | Fri 2 Apr 2021 | 32-0 v Mansfield TownMansfield Town 0-2 Leyton Orient | Sky Bet League Two |
| 27 | Mon 5 Apr 2021 | 3 0-0 v WalsallLeyton Orient 0-0 Walsall | Sky Bet League Two |
| 28 | Sat 10 Apr 2021 | 30-1 v Cheltenham TownCheltenham Town 1-0 Leyton Orient | Sky Bet League Two |
| 29 | Sat 1 May 2021 | 32-3 v Carlisle UnitedLeyton Orient 2-3 Carlisle United | Sky Bet League Two |
| 30 | Sat 8 May 2021 | 30-3 v Salford CitySalford City 3-0 Leyton Orient | Sky Bet League Two |
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