| 1 | Sat 7 Aug 2021 | 21-1 v Salford CitySalford City 1-1 Leyton Orient | Sky Bet League Two |
| 2 | Wed 11 Aug 2021 | 21-1 v Queens Park RangersLeyton Orient 1-1 Queens Park Rangers | Carabao Cup First Round |
| 3 | Sat 14 Aug 2021 | 2 3-0 v Exeter CityLeyton Orient 3-0 Exeter City | Sky Bet League Two |
| 4 | Sat 21 Aug 2021 | 21-1 v Carlisle UnitedCarlisle United 1-1 Leyton Orient | Sky Bet League Two |
| 5 | Tue 24 Aug 2021 | 20-2 v Harrogate TownLeyton Orient 0-2 Harrogate Town | Sky Bet League Two |
| 6 | Sat 28 Aug 2021 | 2 2-0 v Bradford CityLeyton Orient 2-0 Bradford City | Sky Bet League Two |
| 7 | Sat 4 Sep 2021 | 2 2-2 v Newport CountyNewport County 2-2 Leyton Orient | Sky Bet League Two |
| 8 | Sat 11 Sep 2021 | 2 4-0 v Oldham AthleticLeyton Orient 4-0 Oldham Athletic | Sky Bet League Two |
| 9 | Sat 18 Sep 2021 | 23-1 v Bristol RoversBristol Rovers 1-3 Leyton Orient | Sky Bet League Two |
| 10 | Sat 25 Sep 2021 | 2 0-0 v Mansfield TownLeyton Orient 0-0 Mansfield Town | Sky Bet League Two |
| 11 | Sat 2 Oct 2021 | 2 2-3 v Port ValePort Vale 3-2 Leyton Orient | Sky Bet League Two |
| 12 | Tue 5 Oct 2021 | 24-0 v Crawley TownCrawley Town 0-4 Leyton Orient | Papa John’s Trophy |
| 13 | Sat 16 Oct 2021 | 20-0 v WalsallLeyton Orient 0-0 Walsall | Sky Bet League Two |
| 14 | Tue 19 Oct 2021 | 21-1 v Forest Green RoversLeyton Orient 1-1 Forest Green Rovers | Sky Bet League Two |
| 15 | Sat 23 Oct 2021 | 20-0 v StevenageStevenage 0-0 Leyton Orient | Sky Bet League Two |
| 16 | Sat 30 Oct 2021 | 25-0 v Hartlepool UnitedLeyton Orient 5-0 Hartlepool United | Sky Bet League Two |
| 17 | Sat 6 Nov 2021 | 2 1-0 v Ebbsfleet UnitedLeyton Orient 1-0 Ebbsfleet United | Emirates FA Cup First Round |
| 18 | Sat 13 Nov 2021 | 22-2 v RochdaleRochdale 2-2 Leyton Orient | Sky Bet League Two |
| 19 | Sat 20 Nov 2021 | 24-1 v Sutton UnitedLeyton Orient 4-1 Sutton United | Sky Bet League Two |
| 20 | Tue 23 Nov 2021 | 21-1 v Scunthorpe UnitedScunthorpe United 1-1 Leyton Orient | Sky Bet League Two |
| 21 | Sat 27 Nov 2021 | 20-1 v Northampton TownNorthampton Town 1-0 Leyton Orient | Sky Bet League Two |
| 22 | Sat 4 Dec 2021 | 24-0 v Tranmere RoversLeyton Orient 4-0 Tranmere Rovers | Emirates FA Cup Second Round |
| 23 | Tue 7 Dec 2021 | 24-1 v Swindon TownLeyton Orient 4-1 Swindon Town | Sky Bet League Two |
| 24 | Sat 11 Dec 2021 | 21-2 v Crawley TownLeyton Orient 1-2 Crawley Town | Sky Bet League Two |
| 25 | Sat 7 May 2022 | 20-1 v Tranmere RoversLeyton Orient 0-1 Tranmere Rovers | Sky Bet League Two |
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