| 1 | Tue 8 Oct 2019 | 110-3 v AFC WimbledonAFC Wimbledon 3-0 Leyton Orient | Leasing.com Trophy Southern Group C |
| 2 | Sat 12 Oct 2019 | 113-1 v WalsallLeyton Orient 3-1 Walsall | Sky Bet League Two |
| 3 | Sat 19 Oct 2019 | 11 4-0 v Grimsby TownGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 4 | Tue 22 Oct 2019 | 110-4 v Plymouth ArgylePlymouth Argyle 4-0 Leyton Orient | Sky Bet League Two |
| 5 | Sat 26 Oct 2019 | 111-1 v Carlisle UnitedLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 6 | Sat 2 Nov 2019 | 110-1 v MorecambeMorecambe 1-0 Leyton Orient | Sky Bet League Two |
| 7 | Sun 10 Nov 2019 | 111-2 v Maldon & TiptreeLeyton Orient 1-2 Maldon & Tiptree | Emirates FA Cup First Round |
| 8 | Thu 26 Dec 2019 | 111-3 v Colchester UnitedLeyton Orient 1-3 Colchester United | Sky Bet League Two |
| 9 | Tue 21 Jan 2020 | 11 1-1 v Northampton TownLeyton Orient 1-1 Northampton Town | Sky Bet League Two |
| 10 | Tue 11 Feb 2020 | 112-1 v Mansfield TownLeyton Orient 2-1 Mansfield Town | Sky Bet League Two |
| 11 | Sat 15 Feb 2020 | 111-2 v Cheltenham TownCheltenham Town 2-1 Leyton Orient | Sky Bet League Two |
| 12 | Sat 7 Mar 2020 | 11 2-1 v Cambridge UnitedLeyton Orient 2-1 Cambridge United | Sky Bet League Two |
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