| 1 | Tue 15 Sep 2020 | 203-2 v Plymouth ArgyleLeyton Orient 3-2 Plymouth Argyle | Carabao Cup Second Round |
| 2 | Sat 19 Sep 2020 | 20 2-2 v Mansfield TownLeyton Orient 2-2 Mansfield Town | Sky Bet League Two |
| 3 | Sat 3 Oct 2020 | 20 0-2 v Cheltenham TownLeyton Orient 0-2 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 17 Oct 2020 | 202-3 v Grimsby TownLeyton Orient 2-3 Grimsby Town | Sky Bet League Two |
| 5 | Tue 20 Oct 2020 | 201-0 v Tranmere RoversTranmere Rovers 0-1 Leyton Orient | Sky Bet League Two |
| 6 | Sat 24 Oct 2020 | 202-0 v StevenageStevenage 0-2 Leyton Orient | Sky Bet League Two |
| 7 | Tue 3 Nov 2020 | 201-2 v Forest Green RoversForest Green Rovers 2-1 Leyton Orient | Sky Bet League Two |
| 8 | Sat 28 Nov 2020 | 203-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League Two |
| 9 | Sat 5 Dec 2020 | 200-2 v Scunthorpe UnitedScunthorpe United 2-0 Leyton Orient | Sky Bet League Two |
| 10 | Tue 8 Dec 2020 | 201-2 v Bristol RoversLeyton Orient 1-2 Bristol Rovers | Papa John’s Trophy Second Round |
| 11 | Tue 15 Dec 2020 | 20 1-2 v MorecambeMorecambe 2-1 Leyton Orient | Sky Bet League Two |
| 12 | Sat 19 Dec 2020 | 201-2 v Crawley TownLeyton Orient 1-2 Crawley Town | Sky Bet League Two |
| 13 | Sat 26 Dec 2020 | 201-2 v Cambridge UnitedCambridge United 2-1 Leyton Orient | Sky Bet League Two |
| 14 | Tue 29 Dec 2020 | 202-0 v Southend UnitedLeyton Orient 2-0 Southend United | Sky Bet League Two |
| 15 | Sat 2 Jan 2021 | 201-0 v Salford CityLeyton Orient 1-0 Salford City | Sky Bet League Two |
| 16 | Sat 16 Jan 2021 | 20 2-0 v MorecambeLeyton Orient 2-0 Morecambe | Sky Bet League Two |
| 17 | Sat 23 Jan 2021 | 200-1 v Forest Green RoversLeyton Orient 0-1 Forest Green Rovers | Sky Bet League Two |
| 18 | Sat 30 Jan 2021 | 200-2 v Bolton WanderersBolton Wanderers 2-0 Leyton Orient | Sky Bet League Two |
| 19 | Tue 2 Feb 2021 | 200-0 v Crawley TownCrawley Town 0-0 Leyton Orient | Sky Bet League Two |
| 20 | Tue 20 Apr 2021 | 202-4 v Cambridge UnitedLeyton Orient 2-4 Cambridge United | Sky Bet League Two |
| 21 | Sat 24 Apr 2021 | 201-2 v Southend UnitedSouthend United 2-1 Leyton Orient | Sky Bet League Two |
| 22 | Sat 8 May 2021 | 200-3 v Salford CitySalford City 3-0 Leyton Orient | Sky Bet League Two |
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