| 1 | Sat 6 Jul 2019 | 145-0 v Harlow TownHarlow Town 0-5 Leyton Orient | Friendly |
| 2 | Tue 13 Aug 2019 | 140-2 v Plymouth ArgylePlymouth Argyle 2-0 Leyton Orient | Carabao Cup First Round |
| 3 | Sat 24 Aug 2019 | 142-3 v Crawley TownLeyton Orient 2-3 Crawley Town | Sky Bet League Two |
| 4 | Sat 31 Aug 2019 | 141-1 v Salford CitySalford City 1-1 Leyton Orient | Sky Bet League Two |
| 5 | Tue 3 Sep 2019 | 142-0 v Southend UnitedLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 6 | Tue 8 Oct 2019 | 140-3 v AFC WimbledonAFC Wimbledon 3-0 Leyton Orient | Leasing.com Trophy Southern Group C |
| 7 | Sat 12 Oct 2019 | 143-1 v WalsallLeyton Orient 3-1 Walsall | Sky Bet League Two |
| 8 | Sat 14 Dec 2019 | 140-0 v Bradford CityLeyton Orient 0-0 Bradford City | Sky Bet League Two |
| 9 | Sat 21 Dec 2019 | 14 3-2 v Cambridge UnitedCambridge United 2-3 Leyton Orient | Sky Bet League Two |
| 10 | Sun 29 Dec 2019 | 141-1 v Newport CountyNewport County 1-1 Leyton Orient | Sky Bet League Two |
| 11 | Wed 1 Jan 2020 | 14 0-1 v WalsallWalsall 1-0 Leyton Orient | Sky Bet League Two |
| 12 | Sat 11 Jan 2020 | 141-1 v Grimsby TownLeyton Orient 1-1 Grimsby Town | Sky Bet League Two |
| 13 | Sat 18 Jan 2020 | 14 0-1 v Port ValePort Vale 1-0 Leyton Orient | Sky Bet League Two |
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