| 1 | Sat 6 Jul 2019 | 35-0 v Harlow TownHarlow Town 0-5 Leyton Orient | Friendly |
| 2 | Tue 13 Aug 2019 | 30-2 v Plymouth ArgylePlymouth Argyle 2-0 Leyton Orient | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 30-0 v StevenageLeyton Orient 0-0 Stevenage | Sky Bet League Two |
| 4 | Tue 20 Aug 2019 | 33-2 v Mansfield TownMansfield Town 2-3 Leyton Orient | Sky Bet League Two |
| 5 | Sat 7 Sep 2019 | 31-3 v Swindon TownLeyton Orient 1-3 Swindon Town | Sky Bet League Two |
| 6 | Sat 14 Sep 2019 | 32-2 v Exeter CityExeter City 2-2 Leyton Orient | Sky Bet League Two |
| 7 | Tue 17 Sep 2019 | 31-2 v Crewe AlexandraLeyton Orient 1-2 Crewe Alexandra | Sky Bet League Two |
| 8 | Sat 21 Sep 2019 | 31-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 9 | Sat 28 Sep 2019 | 33-3 v Port ValeLeyton Orient 3-3 Port Vale | Sky Bet League Two |
| 10 | Sat 5 Oct 2019 | 3 1-0 v Northampton TownNorthampton Town 0-1 Leyton Orient | Sky Bet League Two |
| 11 | Sat 12 Oct 2019 | 33-1 v WalsallLeyton Orient 3-1 Walsall | Sky Bet League Two |
| 12 | Sat 19 Oct 2019 | 34-0 v Grimsby TownGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 13 | Tue 22 Oct 2019 | 30-4 v Plymouth ArgylePlymouth Argyle 4-0 Leyton Orient | Sky Bet League Two |
| 14 | Sat 26 Oct 2019 | 31-1 v Carlisle UnitedLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 15 | Sat 2 Nov 2019 | 30-1 v MorecambeMorecambe 1-0 Leyton Orient | Sky Bet League Two |
| 16 | Sun 10 Nov 2019 | 31-2 v Maldon & TiptreeLeyton Orient 1-2 Maldon & Tiptree | Emirates FA Cup First Round |
| 17 | Sat 15 Feb 2020 | 31-2 v Cheltenham TownCheltenham Town 2-1 Leyton Orient | Sky Bet League Two |
| 18 | Sat 7 Mar 2020 | 32-1 v Cambridge UnitedLeyton Orient 2-1 Cambridge United | Sky Bet League Two |
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