| 1 | Tue 15 Sep 2020 | 173-2 v Plymouth ArgyleLeyton Orient 3-2 Plymouth Argyle | Carabao Cup Second Round |
| 2 | Sat 19 Sep 2020 | 172-2 v Mansfield TownLeyton Orient 2-2 Mansfield Town | Sky Bet League Two |
| 3 | Sat 3 Oct 2020 | 170-2 v Cheltenham TownLeyton Orient 0-2 Cheltenham Town | Sky Bet League Two |
| 4 | Tue 6 Oct 2020 | 172-0 v AFC WimbledonLeyton Orient 2-0 AFC Wimbledon | Papa John’s Trophy Group 10 |
| 5 | Sat 10 Oct 2020 | 17 1-1 v BarrowBarrow 1-1 Leyton Orient | Sky Bet League Two |
| 6 | Sat 24 Oct 2020 | 172-0 v StevenageStevenage 0-2 Leyton Orient | Sky Bet League Two |
| 7 | Tue 27 Oct 2020 | 171-1 v Exeter CityLeyton Orient 1-1 Exeter City | Sky Bet League Two |
| 8 | Sat 31 Oct 2020 | 174-0 v Bolton WanderersLeyton Orient 4-0 Bolton Wanderers | Sky Bet League Two |
| 9 | Tue 3 Nov 2020 | 171-2 v Forest Green RoversForest Green Rovers 2-1 Leyton Orient | Sky Bet League Two |
| 10 | Tue 10 Nov 2020 | 171-3 v Charlton AthleticCharlton Athletic 3-1 Leyton Orient | Papa John’s Trophy Group 10 |
| 11 | Sat 14 Nov 2020 | 171-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 12 | Sat 21 Nov 2020 | 173-0 v Harrogate TownLeyton Orient 3-0 Harrogate Town | Sky Bet League Two |
| 13 | Tue 24 Nov 2020 | 171-0 v Bradford CityLeyton Orient 1-0 Bradford City | Sky Bet League Two |
| 14 | Sat 28 Nov 2020 | 173-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League Two |
| 15 | Sat 5 Dec 2020 | 170-2 v Scunthorpe UnitedScunthorpe United 2-0 Leyton Orient | Sky Bet League Two |
| 16 | Tue 15 Dec 2020 | 171-2 v MorecambeMorecambe 2-1 Leyton Orient | Sky Bet League Two |
| 17 | Sat 26 Dec 2020 | 171-2 v Cambridge UnitedCambridge United 2-1 Leyton Orient | Sky Bet League Two |
| 18 | Sat 23 Jan 2021 | 170-1 v Forest Green RoversLeyton Orient 0-1 Forest Green Rovers | Sky Bet League Two |
| 19 | Tue 23 Mar 2021 | 171-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League Two |
| 20 | Sat 27 Mar 2021 | 172-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Sky Bet League Two |
| 21 | Mon 5 Apr 2021 | 170-0 v WalsallLeyton Orient 0-0 Walsall | Sky Bet League Two |
| 22 | Tue 13 Apr 2021 | 172-2 v Harrogate TownHarrogate Town 2-2 Leyton Orient | Sky Bet League Two |
| 23 | Sat 17 Apr 2021 | 172-0 v BarrowLeyton Orient 2-0 Barrow | Sky Bet League Two |
| 24 | Tue 20 Apr 2021 | 172-4 v Cambridge UnitedLeyton Orient 2-4 Cambridge United | Sky Bet League Two |
| 25 | Sat 24 Apr 2021 | 171-2 v Southend UnitedSouthend United 2-1 Leyton Orient | Sky Bet League Two |
| 26 | Sat 1 May 2021 | 17 2-3 v Carlisle UnitedLeyton Orient 2-3 Carlisle United | Sky Bet League Two |
| 27 | Sat 8 May 2021 | 170-3 v Salford CitySalford City 3-0 Leyton Orient | Sky Bet League Two |
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