| 1 | Sat 6 Jul 2019 | 125-0 v Harlow TownHarlow Town 0-5 Leyton Orient | Friendly |
| 2 | Sat 3 Aug 2019 | 121-0 v Cheltenham TownLeyton Orient 1-0 Cheltenham Town | Sky Bet League Two |
| 3 | Tue 3 Sep 2019 | 122-0 v Southend UnitedLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 4 | Tue 8 Oct 2019 | 120-3 v AFC WimbledonAFC Wimbledon 3-0 Leyton Orient | Leasing.com Trophy Southern Group C |
| 5 | Sun 10 Nov 2019 | 121-2 v Maldon & TiptreeLeyton Orient 1-2 Maldon & Tiptree | Emirates FA Cup First Round |
| 6 | Sat 14 Dec 2019 | 120-0 v Bradford CityLeyton Orient 0-0 Bradford City | Sky Bet League Two |
| 7 | Sat 21 Dec 2019 | 123-2 v Cambridge UnitedCambridge United 2-3 Leyton Orient | Sky Bet League Two |
| 8 | Thu 26 Dec 2019 | 121-3 v Colchester UnitedLeyton Orient 1-3 Colchester United | Sky Bet League Two |
| 9 | Sun 29 Dec 2019 | 121-1 v Newport CountyNewport County 1-1 Leyton Orient | Sky Bet League Two |
| 10 | Wed 1 Jan 2020 | 120-1 v WalsallWalsall 1-0 Leyton Orient | Sky Bet League Two |
| 11 | Sat 11 Jan 2020 | 121-1 v Grimsby TownLeyton Orient 1-1 Grimsby Town | Sky Bet League Two |
| 12 | Sat 18 Jan 2020 | 120-1 v Port ValePort Vale 1-0 Leyton Orient | Sky Bet League Two |
| 13 | Tue 21 Jan 2020 | 121-1 v Northampton TownLeyton Orient 1-1 Northampton Town | Sky Bet League Two |
| 14 | Sat 25 Jan 2020 | 122-1 v Newport CountyLeyton Orient 2-1 Newport County | Sky Bet League Two |
| 15 | Tue 28 Jan 2020 | 120-2 v Crewe AlexandraCrewe Alexandra 2-0 Leyton Orient | Sky Bet League Two |
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