| 1 | Tue 15 Sep 2020 | 233-2 v Plymouth ArgyleLeyton Orient 3-2 Plymouth Argyle | Carabao Cup Second Round |
| 2 | Tue 13 Oct 2020 | 231-2 v WalsallWalsall 2-1 Leyton Orient | Sky Bet League Two |
| 3 | Sat 17 Oct 2020 | 232-3 v Grimsby TownLeyton Orient 2-3 Grimsby Town | Sky Bet League Two |
| 4 | Tue 3 Nov 2020 | 23 1-2 v Forest Green RoversForest Green Rovers 2-1 Leyton Orient | Sky Bet League Two |
| 5 | Tue 10 Nov 2020 | 231-3 v Charlton AthleticCharlton Athletic 3-1 Leyton Orient | Papa John’s Trophy Group 10 |
| 6 | Tue 8 Dec 2020 | 23 1-2 v Bristol RoversLeyton Orient 1-2 Bristol Rovers | Papa John’s Trophy Second Round |
| 7 | Sat 27 Feb 2021 | 231-3 v Tranmere RoversLeyton Orient 1-3 Tranmere Rovers | Sky Bet League Two |
| 8 | Tue 2 Mar 2021 | 231-0 v Grimsby TownGrimsby Town 0-1 Leyton Orient | Sky Bet League Two |
| 9 | Sat 6 Mar 2021 | 23 0-4 v Exeter CityExeter City 4-0 Leyton Orient | Sky Bet League Two |
| 10 | Tue 9 Mar 2021 | 23 0-0 v StevenageLeyton Orient 0-0 Stevenage | Sky Bet League Two |
| 11 | Sat 13 Mar 2021 | 231-1 v Scunthorpe UnitedLeyton Orient 1-1 Scunthorpe United | Sky Bet League Two |
| 12 | Sat 20 Mar 2021 | 231-0 v Newport CountyNewport County 0-1 Leyton Orient | Sky Bet League Two |
| 13 | Tue 23 Mar 2021 | 231-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League Two |
| 14 | Sat 27 Mar 2021 | 232-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Sky Bet League Two |
| 15 | Fri 2 Apr 2021 | 232-0 v Mansfield TownMansfield Town 0-2 Leyton Orient | Sky Bet League Two |
| 16 | Mon 5 Apr 2021 | 230-0 v WalsallLeyton Orient 0-0 Walsall | Sky Bet League Two |
| 17 | Sat 10 Apr 2021 | 23 0-1 v Cheltenham TownCheltenham Town 1-0 Leyton Orient | Sky Bet League Two |
| 18 | Sat 17 Apr 2021 | 232-0 v BarrowLeyton Orient 2-0 Barrow | Sky Bet League Two |
| 19 | Tue 20 Apr 2021 | 23 2-4 v Cambridge UnitedLeyton Orient 2-4 Cambridge United | Sky Bet League Two |
| 20 | Sat 1 May 2021 | 232-3 v Carlisle UnitedLeyton Orient 2-3 Carlisle United | Sky Bet League Two |
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