| 1 | Sat 16 Sep 2023 | 161-1 v Peterborough UnitedPeterborough United 1-1 Leyton Orient | Sky Bet League One |
| 2 | Sat 23 Sep 2023 | 161-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 3 | Sat 30 Sep 2023 | 160-1 v Fleetwood TownFleetwood Town 1-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 7 Oct 2023 | 162-1 v ReadingLeyton Orient 2-1 Reading | Sky Bet League One |
| 5 | Sat 14 Oct 2023 | 161-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League One |
| 6 | Sat 21 Oct 2023 | 161-1 v BarnsleyLeyton Orient 1-1 Barnsley | Sky Bet League One |
| 7 | Tue 24 Oct 2023 | 162-2 v Northampton TownNorthampton Town 2-2 Leyton Orient | Sky Bet League One |
| 8 | Sat 28 Oct 2023 | 160-0 v Burton AlbionBurton Albion 0-0 Leyton Orient | Sky Bet League One |
| 9 | Sat 4 Nov 2023 | 163-1 v Carlisle UnitedLeyton Orient 3-1 Carlisle United | Emirates FA Cup First Round |
| 10 | Tue 7 Nov 2023 | 161-2 v PortsmouthLeyton Orient 1-2 Portsmouth | EFL Trophy |
| 11 | Sat 11 Nov 2023 | 162-3 v Oxford UnitedLeyton Orient 2-3 Oxford United | Sky Bet League One |
| 12 | Tue 21 Nov 2023 | 160-1 v Lincoln CityLeyton Orient 0-1 Lincoln City | Sky Bet League One |
| 13 | Sat 25 Nov 2023 | 161-1 v Wigan AthleticLeyton Orient 1-1 Wigan Athletic | Sky Bet League One |
| 14 | Tue 28 Nov 2023 | 161-1 v Bristol RoversBristol Rovers 1-1 Leyton Orient | Sky Bet League One |
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