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 |