| 1 | Sat 3 Aug 2019 | 271-0 v Cheltenham TownLeyton Orient 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 270-3 v Macclesfield TownMacclesfield Town 3-0 Leyton Orient | Sky Bet League Two |
| 3 | Sat 24 Aug 2019 | 272-3 v Crawley TownLeyton Orient 2-3 Crawley Town | Sky Bet League Two |
| 4 | Tue 3 Sep 2019 | 272-0 v Southend UnitedLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 5 | Sat 14 Sep 2019 | 272-2 v Exeter CityExeter City 2-2 Leyton Orient | Sky Bet League Two |
| 6 | Sat 21 Sep 2019 | 271-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 7 | Tue 8 Oct 2019 | 270-3 v AFC WimbledonAFC Wimbledon 3-0 Leyton Orient | Leasing.com Trophy Southern Group C |
| 8 | Sat 12 Oct 2019 | 273-1 v WalsallLeyton Orient 3-1 Walsall | Sky Bet League Two |
| 9 | Sat 19 Oct 2019 | 274-0 v Grimsby TownGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 10 | Tue 22 Oct 2019 | 270-4 v Plymouth ArgylePlymouth Argyle 4-0 Leyton Orient | Sky Bet League Two |
| 11 | Sun 10 Nov 2019 | 271-2 v Maldon & TiptreeLeyton Orient 1-2 Maldon & Tiptree | Emirates FA Cup First Round |
| 12 | Sat 16 Nov 2019 | 270-2 v Scunthorpe UnitedLeyton Orient 0-2 Scunthorpe United | Sky Bet League Two |
| 13 | Sat 23 Nov 2019 | 272-4 v Forest Green RoversLeyton Orient 2-4 Forest Green Rovers | Sky Bet League Two |
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