Head to Head
| England League 2 | 2023/04/18 18:45 | Gillingham v Leyton Orient | W | 2-0 |
| England League 2 | 2022/10/25 18:45 | Leyton Orient v Gillingham | L | 2-0 |
| Club Friendly List | 2021/07/31 13:00 | Leyton Orient v Gillingham | L | 2-0 |
| England FA Cup | 2017/11/04 15:00 | Gillingham v Leyton Orient | W | 2-1 |
| England League 1 | 2015/04/06 14:00 | Leyton Orient v Gillingham | D | 3-3 |
| England EFL Trophy | 2014/12/06 15:00 | Gillingham v Leyton Orient | W | 1-0 |
| England League 1 | 2014/11/15 15:00 | Gillingham v Leyton Orient | W | 3-2 |
Home History
| England League 2 | 2023/09/02 14:00 | Grimsby v Gillingham | L | 2-0 |
| England EFL Cup | 2023/08/29 18:45 | Luton v Gillingham | L | 3-2 |
| England League 2 | 2023/08/26 14:00 | Gillingham v Colchester | L | 0-3 |
| England League 2 | 2023/08/19 14:00 | Crawley Town v Gillingham | W | 0-1 |
| England League 2 | 2023/08/15 18:45 | Sutton Utd v Gillingham | W | 0-1 |
| England League 2 | 2023/08/12 14:00 | Gillingham v Accrington Stanley | W | 1-0 |
| England EFL Cup | 2023/08/08 18:45 | Gillingham v Southampton | W | 3-1 |
| England League 2 | 2023/08/05 14:00 | Stockport v Gillingham | W | 0-1 |
Away History
| England League 1 | 2023/09/02 14:00 | Leyton Orient v Stevenage | L | 0-3 |
| England League 1 | 2023/08/26 14:00 | Leyton Orient v Cambridge Utd | W | 2-0 |
| England League 1 | 2023/08/19 14:00 | Blackpool v Leyton Orient | D | 0-0 |
| England League 1 | 2023/08/15 18:45 | Wycombe v Leyton Orient | L | 3-2 |
| England League 1 | 2023/08/12 14:00 | Leyton Orient v Portsmouth | L | 0-4 |
| England EFL Cup | 2023/08/08 18:45 | Plymouth v Leyton Orient | L | 2-0 |
| England League 1 | 2023/08/05 14:00 | Charlton v Leyton Orient | L | 1-0 |
| Club Friendly List | 2023/08/01 18:45 | Bishop's Stortford v Leyton Orient | L | 1-0 |