Saturday 15 August
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |   Leyton Orient vs Sheffield Wednesday | 1 - 2 | League One Stage : MD1 | Matchroom Stadium |
Saturday 22 August
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Wigan vs Leyton Orient | 0 - 2 | League One Stage : MD2 | DW Stadium |
Saturday 29 August
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Leyton Orient vs Barnsley | 1 - 3 | League One Stage : MD3 | Matchroom Stadium |
Tuesday 1 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 |  Bromley vs Leyton Orient | 0 - 5 | League One Stage : MD4 | Hayes Lane |
Saturday 5 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Luton vs Leyton Orient | 1 - 1 | League One Stage : MD5 | Kenilworth Road |
Saturday 12 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 12h30 |  Leyton Orient vs Wycombe | 2 - 3 | League One Stage : MD6 | Matchroom Stadium |
Tuesday 15 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h00 |  Leyton Orient vs Arsenal U21 | 1 - 2 | EFL Trophy Group South Stage : MD6 | Brisbane Road |
Saturday 19 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Leyton Orient vs Stevenage | - | League One Stage : MD7 | Matchroom Stadium |
Saturday 26 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Mansfield Town vs Leyton Orient | - | League One Stage : MD8 | Field Mill |
Saturday 3 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Leyton Orient vs Plymouth | - | League One Stage : MD9 | Matchroom Stadium |
Saturday 10 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Bradford vs Leyton Orient | - | League One Stage : MD10 | Valley Parade |
Saturday 17 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Leyton Orient vs Blackpool | - | League One Stage : MD11 | Matchroom Stadium |
Wednesday 21 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h00 |  Reading vs Leyton Orient | - | League One Stage : MD12 | Madejski Stadium |
Saturday 24 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Burton Albion vs Leyton Orient | - | League One Stage : MD13 | Pirelli Stadium |
Saturday 31 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 13h30 |  Leyton Orient vs Cambridge United | - | League One Stage : MD14 | Matchroom Stadium |
Tuesday 10 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h00 |  Barnet vs Leyton Orient | - | EFL Trophy Group South Stage : MD6 | The Hive Stadium |
Saturday 14 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Doncaster vs Leyton Orient | - | League One Stage : MD15 | Keepmoat Stadium |
Saturday 21 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Leyton Orient vs AFC Wimbledon | - | League One Stage : MD16 | Matchroom Stadium |
Saturday 28 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Stockport County vs Leyton Orient | - | League One Stage : MD17 | Edgeley Park |
Tuesday 1 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 |  Leyton Orient vs Peterborough | - | League One Stage : MD18 | Matchroom Stadium |
Saturday 12 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Huddersfield vs Leyton Orient | - | League One Stage : MD19 | John Smith's Stadium |
Saturday 19 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Leyton Orient vs Notts County | - | League One Stage : MD20 | Matchroom Stadium |
Saturday 26 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Milton Keynes Dons vs Leyton Orient | - | League One Stage : MD21 | Stadium MK |
Tuesday 29 December
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 |  Leyton Orient vs Leicester | - | League One Stage : MD22 | Matchroom Stadium |
Friday 1 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 |  Leyton Orient vs Oxford United | - | League One Stage : MD23 | Matchroom Stadium |
Saturday 9 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Notts County vs Leyton Orient | - | League One Stage : MD24 | Meadow Lane |
Saturday 16 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Blackpool vs Leyton Orient | - | League One Stage : MD25 | Bloomfield Road |
Tuesday 19 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 | Leyton Orient vs Reading | - | League One Stage : MD26 | Brisbane Road |
Saturday 23 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Leyton Orient vs Burton Albion | - | League One Stage : MD27 | Brisbane Road |
Saturday 30 January
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Cambridge United vs Leyton Orient | - | League One Stage : MD28 | Abbey Stadium |
Saturday 6 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Barnsley vs Leyton Orient | - | League One Stage : MD29 | Oakwell |
Tuesday 9 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 20h45 | Leyton Orient vs Bromley | - | League One Stage : MD30 | Brisbane Road |
Saturday 13 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Leyton Orient vs Luton | - | League One Stage : MD31 | Brisbane Road |
Saturday 20 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Wycombe vs Leyton Orient | - | League One Stage : MD32 | Adams Park |
Saturday 27 February
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Leyton Orient vs Doncaster | - | League One Stage : MD33 | Brisbane Road |
Saturday 6 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Sheffield Wednesday vs Leyton Orient | - | League One Stage : MD34 | Hillsborough |
Saturday 13 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Leyton Orient vs Wigan | - | League One Stage : MD35 | Brisbane Road |
Saturday 20 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | AFC Wimbledon vs Leyton Orient | - | League One Stage : MD36 | The Cherry Red Records Stadium |
Friday 26 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 16h00 | Oxford United vs Leyton Orient | - | League One Stage : MD37 | Kassam Stadium |
Monday 29 March
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Leyton Orient vs Huddersfield | - | League One Stage : MD38 | Brisbane Road |
Saturday 3 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Leicester vs Leyton Orient | - | League One Stage : MD39 | King Power Stadium |
Saturday 10 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Leyton Orient vs Milton Keynes Dons | - | League One Stage : MD40 | Brisbane Road |
Tuesday 13 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 | Leyton Orient vs Mansfield Town | - | League One Stage : MD41 | Brisbane Road |
Saturday 17 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Stevenage vs Leyton Orient | - | League One Stage : MD42 | Lamex Stadium |
Saturday 24 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Leyton Orient vs Bradford | - | League One Stage : MD43 | Brisbane Road |
Tuesday 27 April
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 | Plymouth vs Leyton Orient | - | League One Stage : MD44 | Home Park |
Saturday 1 May
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 | Leyton Orient vs Stockport County | - | League One Stage : MD45 | Brisbane Road |
Saturday 8 May
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 12h30 | Peterborough vs Leyton Orient | - | League One Stage : MD46 | Weston Homes Stadium |