| 1 | Sat 6 Jul 2019 | 175-0 v Harlow TownHarlow Town 0-5 Leyton Orient | Friendly |
| 2 | Sat 10 Aug 2019 | 170-3 v Macclesfield TownMacclesfield Town 3-0 Leyton Orient | Sky Bet League Two |
| 3 | Sat 17 Aug 2019 | 170-0 v StevenageLeyton Orient 0-0 Stevenage | Sky Bet League Two |
| 4 | Sat 31 Aug 2019 | 171-1 v Salford CitySalford City 1-1 Leyton Orient | Sky Bet League Two |
| 5 | Tue 3 Sep 2019 | 172-0 v Southend UnitedLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 6 | Tue 17 Sep 2019 | 171-2 v Crewe AlexandraLeyton Orient 1-2 Crewe Alexandra | Sky Bet League Two |
| 7 | Sat 21 Sep 2019 | 171-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 8 | Sat 28 Sep 2019 | 173-3 v Port ValeLeyton Orient 3-3 Port Vale | Sky Bet League Two |
| 9 | Sat 5 Oct 2019 | 171-0 v Northampton TownNorthampton Town 0-1 Leyton Orient | Sky Bet League Two |
| 10 | Sat 12 Oct 2019 | 17 3-1 v WalsallLeyton Orient 3-1 Walsall | Sky Bet League Two |
| 11 | Sat 19 Oct 2019 | 17 4-0 v Grimsby TownGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 12 | Tue 22 Oct 2019 | 170-4 v Plymouth ArgylePlymouth Argyle 4-0 Leyton Orient | Sky Bet League Two |
| 13 | Sat 26 Oct 2019 | 171-1 v Carlisle UnitedLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 14 | Sat 2 Nov 2019 | 170-1 v MorecambeMorecambe 1-0 Leyton Orient | Sky Bet League Two |
| 15 | Sun 10 Nov 2019 | 17 1-2 v Maldon & TiptreeLeyton Orient 1-2 Maldon & Tiptree | Emirates FA Cup First Round |
| 16 | Sat 16 Nov 2019 | 170-2 v Scunthorpe UnitedLeyton Orient 0-2 Scunthorpe United | Sky Bet League Two |
| 17 | Sat 23 Nov 2019 | 172-4 v Forest Green RoversLeyton Orient 2-4 Forest Green Rovers | Sky Bet League Two |
| 18 | Sat 21 Dec 2019 | 173-2 v Cambridge UnitedCambridge United 2-3 Leyton Orient | Sky Bet League Two |
| 19 | Sun 29 Dec 2019 | 171-1 v Newport CountyNewport County 1-1 Leyton Orient | Sky Bet League Two |
| 20 | Wed 1 Jan 2020 | 170-1 v WalsallWalsall 1-0 Leyton Orient | Sky Bet League Two |
| 21 | Sat 11 Jan 2020 | 171-1 v Grimsby TownLeyton Orient 1-1 Grimsby Town | Sky Bet League Two |
| 22 | Sat 18 Jan 2020 | 170-1 v Port ValePort Vale 1-0 Leyton Orient | Sky Bet League Two |
| 23 | Tue 21 Jan 2020 | 171-1 v Northampton TownLeyton Orient 1-1 Northampton Town | Sky Bet League Two |
| 24 | Sat 25 Jan 2020 | 172-1 v Newport CountyLeyton Orient 2-1 Newport County | Sky Bet League Two |
| 25 | Tue 28 Jan 2020 | 170-2 v Crewe AlexandraCrewe Alexandra 2-0 Leyton Orient | Sky Bet League Two |
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