[1] Leyton Orient 2-0 Gillingham [19] 2022-10-25 18:45
Stadium: Matchroom Stadium Round: 16
Referee: Charles Breakspear Home Manager: Richie Wellens Away Manager: Neil Harris
Head to Head
| Europa - Vennskapskamper | 2021/07/31 13:00 | Leyton Orient v Gillingham | W | 2-0 |
| England - FA Cup | 2017/11/04 15:00 | Gillingham v Leyton Orient | L | 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 | L | 1-0 |
| England - League 1 | 2014/11/15 15:00 | Gillingham v Leyton Orient | L | 3-2 |
Home History
| England - League 2 | 2022/10/22 14:00 | Carlisle v Leyton Orient | W | 2-3 |
| England - EFL Trophy | 2022/10/18 19:30 | Leyton Orient v Chelsea U21 | L | 2-3 |
| England - League 2 | 2022/10/15 14:00 | Leyton Orient v Northampton | D | 0-0 |
| England - League 2 | 2022/10/08 14:00 | Doncaster v Leyton Orient | D | 1-1 |
| England - League 2 | 2022/10/01 14:00 | Leyton Orient v Newport County | L | 1-2 |
| England - League 2 | 2022/09/24 14:00 | Barrow v Leyton Orient | W | 0-2 |
| England - EFL Trophy | 2022/09/20 18:00 | Leyton Orient v Sutton Utd | W | 3-1 |
| England - League 2 | 2022/09/17 14:00 | Leyton Orient v Walsall | W | 1-0 |
Away History
| England - League 2 | 2022/10/22 14:00 | Gillingham v Barrow | D | 1-1 |
| England - League 2 | 2022/10/15 14:00 | Gillingham v Stevenage | D | 1-1 |
| England - EFL Trophy | 2022/10/11 18:45 | Gillingham v Colchester | W | 6-5 |
| England - League 2 | 2022/10/08 14:00 | Crewe v Gillingham | D | 1-1 |
| England - EFL Trophy | 2022/10/04 18:00 | Gillingham v Brighton U21 | W | 3-2 |
| England - League 2 | 2022/10/01 14:00 | Gillingham v Sutton Utd | W | 1-0 |
| England - League 2 | 2022/09/24 14:00 | Hartlepool v Gillingham | D | 0-0 |
| England - League 2 | 2022/09/17 14:00 | Gillingham v Mansfield | L | 0-2 |