| 1 | Tue 10 Nov 2020 | 261-3 v Charlton AthleticCharlton Athletic 3-1 Leyton Orient | Papa John’s Trophy Group 10 |
| 2 | Sat 14 Nov 2020 | 261-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 3 | Sat 21 Nov 2020 | 263-0 v Harrogate TownLeyton Orient 3-0 Harrogate Town | Sky Bet League Two |
| 4 | Tue 24 Nov 2020 | 261-0 v Bradford CityLeyton Orient 1-0 Bradford City | Sky Bet League Two |
| 5 | Sat 28 Nov 2020 | 263-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League Two |
| 6 | Tue 8 Dec 2020 | 26 1-2 v Bristol RoversLeyton Orient 1-2 Bristol Rovers | Papa John’s Trophy Second Round |
| 7 | Tue 15 Dec 2020 | 261-2 v MorecambeMorecambe 2-1 Leyton Orient | Sky Bet League Two |
| 8 | Sat 19 Dec 2020 | 261-2 v Crawley TownLeyton Orient 1-2 Crawley Town | Sky Bet League Two |
| 9 | Tue 29 Dec 2020 | 262-0 v Southend UnitedLeyton Orient 2-0 Southend United | Sky Bet League Two |
| 10 | Sat 16 Jan 2021 | 262-0 v MorecambeLeyton Orient 2-0 Morecambe | Sky Bet League Two |
| 11 | Sat 30 Jan 2021 | 260-2 v Bolton WanderersBolton Wanderers 2-0 Leyton Orient | Sky Bet League Two |
| 12 | Tue 2 Feb 2021 | 26 0-0 v Crawley TownCrawley Town 0-0 Leyton Orient | Sky Bet League Two |
| 13 | Sat 27 Feb 2021 | 261-3 v Tranmere RoversLeyton Orient 1-3 Tranmere Rovers | Sky Bet League Two |
| 14 | Tue 2 Mar 2021 | 261-0 v Grimsby TownGrimsby Town 0-1 Leyton Orient | Sky Bet League Two |
| 15 | Sat 13 Mar 2021 | 261-1 v Scunthorpe UnitedLeyton Orient 1-1 Scunthorpe United | Sky Bet League Two |
| 16 | Sat 20 Mar 2021 | 261-0 v Newport CountyNewport County 0-1 Leyton Orient | Sky Bet League Two |
| 17 | Fri 2 Apr 2021 | 262-0 v Mansfield TownMansfield Town 0-2 Leyton Orient | Sky Bet League Two |
| 18 | Mon 5 Apr 2021 | 260-0 v WalsallLeyton Orient 0-0 Walsall | Sky Bet League Two |
| 19 | Sat 10 Apr 2021 | 260-1 v Cheltenham TownCheltenham Town 1-0 Leyton Orient | Sky Bet League Two |
| 20 | Tue 13 Apr 2021 | 262-2 v Harrogate TownHarrogate Town 2-2 Leyton Orient | Sky Bet League Two |
| 21 | Sat 17 Apr 2021 | 262-0 v BarrowLeyton Orient 2-0 Barrow | Sky Bet League Two |
| 22 | Tue 20 Apr 2021 | 262-4 v Cambridge UnitedLeyton Orient 2-4 Cambridge United | Sky Bet League Two |
| 23 | Sat 24 Apr 2021 | 261-2 v Southend UnitedSouthend United 2-1 Leyton Orient | Sky Bet League Two |
| 24 | Sat 8 May 2021 | 260-3 v Salford CitySalford City 3-0 Leyton Orient | Sky Bet League Two |
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