| 1 | Tue 15 Aug 2023 | 4 2-3 v Wycombe WanderersWycombe Wanderers 3-2 Leyton Orient | Sky Bet League One |
| 2 | Sat 19 Aug 2023 | 4 0-0 v BlackpoolBlackpool 0-0 Leyton Orient | Sky Bet League One |
| 3 | Sat 26 Aug 2023 | 42-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 4 | Sat 2 Sep 2023 | 4 0-3 v StevenageLeyton Orient 0-3 Stevenage | Sky Bet League One |
| 5 | Sat 7 Oct 2023 | 42-1 v ReadingLeyton Orient 2-1 Reading | Sky Bet League One |
| 6 | Sat 14 Oct 2023 | 4 1-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League One |
| 7 | Tue 24 Oct 2023 | 4 2-2 v Northampton TownNorthampton Town 2-2 Leyton Orient | Sky Bet League One |
| 8 | Sat 4 Nov 2023 | 43-1 v Carlisle UnitedLeyton Orient 3-1 Carlisle United | Emirates FA Cup First Round |
| 9 | Tue 7 Nov 2023 | 41-2 v PortsmouthLeyton Orient 1-2 Portsmouth | EFL Trophy |
| 10 | Sat 11 Nov 2023 | 42-3 v Oxford UnitedLeyton Orient 2-3 Oxford United | Sky Bet League One |
| 11 | Tue 21 Nov 2023 | 40-1 v Lincoln CityLeyton Orient 0-1 Lincoln City | Sky Bet League One |
| 12 | Sat 25 Nov 2023 | 41-1 v Wigan AthleticLeyton Orient 1-1 Wigan Athletic | Sky Bet League One |
| 13 | Tue 28 Nov 2023 | 4 1-1 v Bristol RoversBristol Rovers 1-1 Leyton Orient | Sky Bet League One |
| 14 | Sun 3 Dec 2023 | 40-1 v ChesterfieldChesterfield 1-0 Leyton Orient | Emirates FA Cup Second Round |
| 15 | Sat 13 Jan 2024 | 43-0 v PortsmouthPortsmouth 0-3 Leyton Orient | Sky Bet League One |
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