| 1 | Sat 3 Aug 2019 | 1-0 v Cheltenham TownLeyton Orient 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 0-3 v Macclesfield TownMacclesfield Town 3-0 Leyton Orient | Sky Bet League Two |
| 3 | Tue 13 Aug 2019 | 0-2 v Plymouth ArgylePlymouth Argyle 2-0 Leyton Orient | Carabao Cup First Round |
| 4 | Tue 20 Aug 2019 | 3-2 v Mansfield TownMansfield Town 2-3 Leyton Orient | Sky Bet League Two |
| 5 | Sat 24 Aug 2019 | 2-3 v Crawley TownLeyton Orient 2-3 Crawley Town | Sky Bet League Two |
| 6 | Sat 31 Aug 2019 | 1-1 v Salford CitySalford City 1-1 Leyton Orient | Sky Bet League Two |
| 7 | Tue 3 Sep 2019 | 2-0 v Southend UnitedLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 8 | Sat 7 Sep 2019 | 1-3 v Swindon TownLeyton Orient 1-3 Swindon Town | Sky Bet League Two |
| 9 | Sat 14 Sep 2019 | 2-2 v Exeter CityExeter City 2-2 Leyton Orient | Sky Bet League Two |
| 10 | Tue 17 Sep 2019 | 1-2 v Crewe AlexandraLeyton Orient 1-2 Crewe Alexandra | Sky Bet League Two |
| 11 | Sat 21 Sep 2019 | 1-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 12 | Sat 28 Sep 2019 | 3-3 v Port ValeLeyton Orient 3-3 Port Vale | Sky Bet League Two |
| 13 | Tue 8 Oct 2019 | 0-3 v AFC WimbledonAFC Wimbledon 3-0 Leyton Orient | Leasing.com Trophy Southern Group C |
| 14 | Sat 19 Oct 2019 | 4-0 v Grimsby TownGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 15 | Tue 22 Oct 2019 | 0-4 v Plymouth ArgylePlymouth Argyle 4-0 Leyton Orient | Sky Bet League Two |
| 16 | Sat 26 Oct 2019 | 1-1 v Carlisle UnitedLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 17 | Sun 10 Nov 2019 | 1-2 v Maldon & TiptreeLeyton Orient 1-2 Maldon & Tiptree | Emirates FA Cup First Round |
| 18 | Sat 16 Nov 2019 | 0-2 v Scunthorpe UnitedLeyton Orient 0-2 Scunthorpe United | Sky Bet League Two |
| 19 | Wed 1 Jan 2020 | 0-1 v WalsallWalsall 1-0 Leyton Orient | Sky Bet League Two |
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