Head to Head
| England National League | 2019/01/26 15:00 | Leyton Orient v Maidstone Utd | L | 3-0 |
| England FA Cup Qualification | 2018/10/20 14:00 | Maidstone Utd v Leyton Orient | W | 2-0 |
| England National League | 2018/08/14 18:45 | Maidstone Utd v Leyton Orient | L | 1-2 |
| England National League | 2017/12/23 15:00 | Maidstone Utd v Leyton Orient | L | 0-2 |
| England National League | 2017/08/12 14:00 | Leyton Orient v Maidstone Utd | L | 2-0 |
Home History
| England National League South | 2022/05/07 14:00 | Maidstone Utd v Hampton & Richmond | W | 2-1 |
| England National League South | 2022/05/02 14:00 | Welling v Maidstone Utd | L | 3-2 |
| England National League South | 2022/04/30 14:00 | Maidstone Utd v Chelmsford | W | 3-1 |
| England National League South | 2022/04/23 14:00 | Hemel Hempstead v Maidstone Utd | W | 0-4 |
| England National League South | 2022/04/18 14:00 | Dartford v Maidstone Utd | W | 0-1 |
| England National League South | 2022/04/09 14:00 | Chippenham Town v Maidstone Utd | W | 1-2 |
| England National League South | 2022/04/02 14:00 | Maidstone Utd v Havant and W | W | 4-0 |
| England National League South | 2022/03/26 15:00 | Maidstone Utd v St Albans | W | 3-2 |
Away History
| Club Friendly List | 2022/07/08 10:00 | Leyton Orient v Peterborough | L | 0-3 |
| Club Friendly List | 2022/07/04 17:30 | Leyton Orient v West Brom | L | 1-2 |
| Club Friendly List | 2022/07/01 18:00 | Haringey Borough v Leyton Orient | W | 1-2 |
| England League 2 | 2022/05/07 14:00 | Leyton Orient v Tranmere | L | 0-1 |
| England League 2 | 2022/04/30 14:00 | Crawley Town v Leyton Orient | W | 0-2 |
| England League 2 | 2022/04/23 14:00 | Leyton Orient v Northampton | L | 2-4 |
| England League 2 | 2022/04/18 14:00 | Swindon v Leyton Orient | W | 1-2 |
| England League 2 | 2022/04/15 14:00 | Leyton Orient v Scunthorpe | W | 3-0 |