Head to Head
| 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
| Club Friendly List | 2021/07/24 14:00 | Maidenhead Utd v Leyton Orient | W | 1-2 |
| Club Friendly List | 2021/07/17 14:00 | Leyton Orient v Tottenham | D | 1-1 |
| Club Friendly List | 2021/07/13 18:00 | Leyton Orient v West Ham | D | 0-0 |
| UK Friendlies | 2021/07/13 18:00 | Leyton Orient v West Ham XI | D | 0-0 |
| Club Friendly List | 2021/07/06 16:00 | Dundee v Leyton Orient | L | 3-0 |
| England League 2 | 2021/05/08 15:00 | Salford City v Leyton Orient | L | 3-0 |
| England League 2 | 2021/05/01 14:00 | Leyton Orient v Carlisle | L | 2-3 |
| England League 2 | 2021/04/24 14:00 | Southend v Leyton Orient | L | 2-1 |
Away History
| Club Friendly List | 2021/07/27 18:00 | Gillingham v Millwall | D | 1-1 |
| Club Friendly List | 2021/07/24 14:00 | Colchester v Gillingham | W | 0-2 |
| UK Friendlies | 2021/07/13 18:00 | Dartford v Gillingham | D | 0-0 |
| Club Friendly List | 2021/07/10 12:00 | Welling v Gillingham | D | 3-3 |
| England League 1 | 2021/05/09 11:00 | Gillingham v Plymouth | W | 1-0 |
| England League 1 | 2021/05/01 14:00 | Burton Albion v Gillingham | D | 1-1 |
| England League 1 | 2021/04/24 14:00 | Gillingham v Northampton | D | 2-2 |
| England League 1 | 2021/04/20 18:45 | Peterborough v Gillingham | W | 0-1 |
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