| 1 | 31/8/2019 | 1-1 v Salford CitySalford City 1-1 Leyton Orient | Sky Bet League Two |
| 2 | 3/9/2019 | 2-0 v Southend UnitedLeyton Orient 2-0 Southend United | Checkatrade Trophy Southern Group C |
| 3 | 7/9/2019 | 1-3 v Swindon TownLeyton Orient 1-3 Swindon Town | Sky Bet League Two |
| 4 | 14/9/2019 | 2-2 v Exeter CityExeter City 2-2 Leyton Orient | Sky Bet League Two |
| 5 | 17/9/2019 | 1-2 v Crewe AlexandraLeyton Orient 1-2 Crewe Alexandra | Sky Bet League Two |
| 6 | 21/9/2019 | 1-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 7 | 28/9/2019 | 3-3 v Port ValeLeyton Orient 3-3 Port Vale | Sky Bet League Two |
| 8 | 5/10/2019 | 1-0 v Northampton TownNorthampton Town 0-1 Leyton Orient | Sky Bet League Two |
| 9 | 8/10/2019 | 0-3 v AFC WimbledonAFC Wimbledon 3-0 Leyton Orient | Checkatrade Trophy Southern Group C |
| 10 | 12/10/2019 | 3-1 v WalsallLeyton Orient 3-1 Walsall | Sky Bet League Two |
| 11 | 19/10/2019 | 4-0 v Grimsby TownGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 12 | 22/10/2019 | 0-4 v Plymouth ArgylePlymouth Argyle 4-0 Leyton Orient | Sky Bet League Two |
| 13 | 26/10/2019 | 1-1 v Carlisle UnitedLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 14 | 2/11/2019 | 0-1 v MorecambeMorecambe 1-0 Leyton Orient | Sky Bet League Two |
| 15 | 10/11/2019 | 1-2 v Maldon & TiptreeLeyton Orient 1-2 Maldon & Tiptree | Emirates FA Cup First Round |
| 16 | 16/11/2019 | 0-2 v Scunthorpe UnitedLeyton Orient 0-2 Scunthorpe United | Sky Bet League Two |
| 17 | 23/11/2019 | 2-4 v Forest Green RoversLeyton Orient 2-4 Forest Green Rovers | Sky Bet League Two |
